Name: 351-83-7|4-Fluoroacetanilide|98%
Brand: Ambeed
SKU: A946810
Price: 14.0 USD
Availability: InStock
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1
[ 108-86-1 ]
[ 351-83-7 ]
[ 330-83-6 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; potassium carbonate; nitrobenzene und Behandeln des Reaktionsprodukts mit wss.-aethanol. Salzsaeure;

Reference： [1]Leonard; Sutton [Journal of the American Chemical Society, 1948, vol. 70, p. 1564,1565]

2
[ 351-83-7 ]
[ 351-84-8 ]

Yield	Reaction Conditions	Operation in experiment
73%	With Lawessons reagent In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	1.1.2. General procedure B General procedure: Compounds 2a-2e, 4a, and 4b were synthesized using a modified procedure.1 Compound 1a-1e, 3a, or 3b (1.0 equiv.) was added to a round-bottom flask. The flask was fitted with a rubber septum, purged with nitrogen gas, then dry THF was added. Lawesson’s reagent (0.7 equiv.) was added then the mixture was stirred at room temperature for 24 h and monitored by TLC. Upon completion the reaction mixture was quenched with H2O and the resulting mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried over anh. Na2SO4, filtered then concentrated in vacuo. The crude mixture was purified by silica gel column chromatography to give the product.
34%	With Lawessons reagent In toluene at 100 - 110℃; for 2h; Inert atmosphere;
	With tetraphosphorus decasulfide; xylene

	With Lawessons reagent In 1,4-dioxane at 110℃;	4. General procedure for the synthesis of thioacetamides (12a-e) General procedure: The acetamides (11a-e, 10mmol) were refluxed with Lawesson’s reagent (7mmol) in dioxane for 3h. After completion of the reaction, dioxane was removed under reduced pressure, water was added and the product was extracted using ethyl acetate. The product was purified using column chromatography on silica gel 60-120 mesh to afford pure 12a-e in good yields.
	With Lawessons reagent In tetrahydrofuran at 20℃; for 24h;	General Procedure B: Synthesis of Thioacetanilides. General procedure: A solution of acetanilides (0.3 M) in THF was mixed with Lawesson's Reagent (0.75-1 eqiv) and stirred at room temperature for 24 h. The reaction mixture was evaporated in vacuo and chromatographed for purification purpose.
	With tetraphosphorus decasulfide; Hexamethyldisiloxane In dichloromethane at 150 - 200℃; Sealed tube; Microwave irradiation;	Fluorothiocetanilides General procedure: Starting fluoroacetanilide derivative(12 mmol), P4S10 (2.28 mmol) and hexamethyldisiloxane, HMDO(20 mmol) were placed in a 10 ml sealed microwave glass tube andsolved with dichloromethane (3 ml). The reaction mixture washeated at 150e200 C for 30e60 min with constant stirring. The reaction progress was monitored by TLC and final products werepurified following procedures published elsewhere [14].

Reference： [1]Lasing, Thitiya; Phumee, Atchara; Siriyasatien, Padet; Chitchak, Kantima; Vanalabhpatana, Parichatr; Mak, Kit-Kay; Hee Ng, Chew; Vilaivan, Tirayut; Khotavivattana, Tanatorn [Bioorganic and Medicinal Chemistry, 2020, vol. 28, # 1]
[2]Song, Shuyi; Hyodo, Tadashi; Ikeda, Hirotaka; Vu, Kim Anh L.; Tang, Yulan; Chan, Erika S.; Otani, Yuko; Inagaki, Satoshi; Yamaguchi, Kentaro; Ohwada, Tomohiko [Journal of Organic Chemistry, 2022, vol. 87, # 3, p. 1641 - 1660]
[3]Kiprianow; Jagupol'skii [Zhurnal Obshchei Khimii, 1950, vol. 20, p. 2111,2114; engl. Ausg. S. 2187, 2190]
[4]Shaik, Thokhir B.; Hussaini, S.M. Ali; Nayak, V. Lakshma; Sucharitha, M. Lakshmi; Malik, M. Shaheer; Kamal, Ahmed [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 11, p. 2549 - 2558]
[5]Aswad, Muhammad; Chiba, Junya; Tomohiro, Takenori; Hatanaka, Yasumaru [Tetrahedron Letters, 2016, vol. 57, # 12, p. 1313 - 1316]
[6]Domínguez, Rodrigo E.; Iriarte, Ana G.; Lezama, José Osvaldo Guy; Robles, Norma Lis [Journal of Molecular Structure, 2020, vol. 1222]

3
[ 351-83-7 ]
[ 364-78-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	With nitric acid; acetic anhydride at 50 - 100℃; for 4h; Flow reactor;	1.b; 2.b; 3.b; 4.b; 5.b; 6.b; 7.b; 8.b; 9.b b. Synthesis of 4-fluoro-2-nitroaniline: Using Corning's high-throughput continuous flow microchannel reactor, based on the molar ratio of p-fluoroacetanilide to nitric acid of 1.0: 1.3, the prepared acetic acid-acetic anhydride solution of p-fluoroacetanilide with a mass concentration of 35% and The mass percentage concentration is 68% nitric acid, and the flow rate of the acetic acid-acetic anhydride solution metering pump of p-fluoroacetanilide is 78.0mL / min, and the flow rate of the nitric acid metering pump is 17.7mL / min. The acetic anhydride solution and nitric acid were separately pumped into Corning ’s high-throughput continuous-flow microchannel reactor with a temperature of 50 ° C and a separate first module-the DC-type preheating module; then preheated through Corning ’s high-throughput continuous The A or B inlet of the flow microchannel reactor enters the second module-the enhanced mass transfer type mixing module. The mixed reaction is performed at a reaction temperature of 50 ° C for 150 s. The mixed liquid from the reaction is from the Corning high-flux continuous flow microchannel The outlet of the reactor flows out; then enter the acid solution hydrolysis reactor, and carry out the hydrolysis reaction at a temperature of 100 ° C for 4h to obtain a product-containing reaction liquid; the product-containing reaction liquid is added to a solution containing 0 ° C to 5 ° C under stirring conditions In the acid water hydrolysis reactor of ice water, stir for 0.5h and then filter. The obtained filter cake is washed with ice water at 0 5 for 2 ~ 3 times until the filter cake is weakly acidic or neutral. Then add appropriate amount of petroleum ether to beat or crush Once, vacuum drying at 50 for 12h to obtain orange solid 4-fluoro-2nitroaniline, yield 93%, liquid phase purity 99.6%.
54%	With nitric acid In acetic acid at 90℃; for 4h;
	With nitric acid; acetic anhydride; acetic acid Kochen des entstandenen Acetylderivats mit konz.Salzsaeure;

	Multi-step reaction with 2 steps 1: nitric acid / 0 - 5 °C 2: 9 M HCl / 0.5 h / Heating
	Multi-step reaction with 2 steps 1: 60percent nitric acid, conc. sulfuric acid / 1.) 0 deg C, 10 min, 2.) RT, 30 min 2: conc. sulfuric acid / 0.25 h / 100 °C
	Multi-step reaction with 2 steps 1: conc. H₂SO₄, conc. HNO₃ / 0 - 3 °C 2: 35percent aq.H₂SO₄ / 1 h / 100 °C
	Multi-step reaction with 2 steps 1: acetic acid anhydride / 0 °C 2: diluted hydrochloric acid
	Multi-step reaction with 2 steps 1: sulfuric acid 2: aqueous hydrochloric acid
	Multi-step reaction with 2 steps 1: (nitration) 2: (hydrolysis)
	Multi-step reaction with 2 steps 1: HNO₃, H₂SO₄ 2: aq. HCl
	Multi-step reaction with 2 steps 1: nitric acid; acetic anhydride / dichloromethane 2: hydrogenchloride / water / Reflux
	Multi-step reaction with 2 steps 1: acetic anhydride; acetic acid; nitric acid / 12 h / 0 - 25 °C 2: hydrogenchloride / water / 4 h / Reflux

Reference： [1]Current Patent Assignee: CHENGDU AIBIKE MEDICINE TECH - CN111018717, 2020, A Location in patent: Paragraph 0015-0023
[2]Leyva, Socorro; Castanedo, Víctor; Leyva, Elisa [Journal of Fluorine Chemistry, 2003, vol. 121, # 2, p. 171 - 175]
[3]van Hove [Bulletin de la Classe des Sciences, Academie Royale de Belgique, 1926, vol. <5>12, p. 811][Chemisches Zentralblatt, 1927, vol. 98, # I, p. 884]
[4]Kuhler; Fryklund; Bergman; Weilitz; Lee; Larsson [Journal of Medicinal Chemistry, 1995, vol. 38, # 25, p. 4906 - 4916]
[5]Monge, Antonio; Palop, Juan A.; Cerain, Adela Lopez de; Senador, Virginia; Martinez-Crespo, Francisko J.; et al. [Journal of Medicinal Chemistry, 1995, vol. 38, # 10, p. 1786 - 1792]
[6]Pujari, H. K.; Sharma, B. R.; Dahiya, Rajender; Kumar, Sudhir; Murakami, Yasuoki; Tani, Masanobu [Journal of Fluorine Chemistry, 1990, vol. 46, # 2, p. 343 - 355]
[7]Swarts [Recueil des Travaux Chimiques des Pays-Bas, 1916, vol. 35, p. 142][Chemisches Zentralblatt, 1913, vol. 84, # II, p. 760]
[8]Wilkinson; Finar [Journal of the Chemical Society, 1948, p. 288,290]
[9]Liedholm,B. [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1976, vol. 30, p. 141 - 149]
[10]Ghosh; Ternai; Whitehouse [Journal of medicinal chemistry, 1972, vol. 15, # 3, p. 255 - 260]
[11]Chopra, Sidharth; Koolpe, Gary A.; Tambo-Ong, Arlyn A.; Matsuyama, Karen N.; Ryan, Kenneth J.; Tran, Tran B.; Doppalapudi, Rupa S.; Riccio, Edward S.; Iyer, Lalitha V.; Green, Carol E.; Wan, Baojie; Franzblau, Scott G.; Madrid, Peter B. [Journal of Medicinal Chemistry, 2012, vol. 55, # 13, p. 6047 - 6060]
[12]Brindisi, Margherita; Brogi, Simone; Maramai, Samuele; Grillo, Alessandro; Borrelli, Giuseppe; Butini, Stefania; Novellino, Ettore; Allarà, Marco; Ligresti, Alessia; Campiani, Giuseppe; Di Marzo, Vincenzo; Gemma, Sandra [RSC Advances, 2016, vol. 6, # 69, p. 64651 - 64664]

4
[ 351-83-7 ]
[ 448-39-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With HNO₃; acetic anhydride; glacial acetic acid at 0 - 25℃; for 12h;
96%	With ammonium molybdate; lithium hydroxide monohydrate; HNO₃ In chloroform for 6h; Heating;
95.9%	Stage #1: N₁-(4-Fluorophenyl)acetamide With sulfuric acid In dichloromethane at 0 - 5℃; for 1h; Stage #2: With HNO₃ In dichloromethane at 5 - 10℃; for 1h;	1.2; 2.2; 3.2 Step 2: Add dichloromethane (20ml) to the flask, add 4-fluoroacetanilide (5g), cool down to 0-5 °C in the refrigeration cycle, add concentrated sulfuric acid (98g) dropwise, the dripping time is about 1 hour, and fuming nitric acid (2.67g) is dripped. During the dripping, the temperature is controlled at 5-10 °C, the dripping time is about 1 hour, and the heat preservation is continued for two hours. Pour the reaction solution slowly into 50ml ice water, let stand to separate the layers, extract the aqueous layer with 30ml dichloromethane, combine the organic layers, dry with anhydrous sodium sulfate and spin dry to obtain 62.0 g of light yellow solid with a yield of 95.9%.

75%	With iron (ΙΙΙ) nitrate nonahydrate; NHPI In 1,2-dichloro-ethane at 50℃; for 10h; regioselective reaction;
58%	With tert.-butylnitrite at 25℃; for 4h;	3 Add 0.2 mmol p-fluoroacetanilide, 0.6 mmol tert-butyl nitrite, 2 mL hexafluoroisopropanol and a No. 5 magnetron into the reactor for mixing, pass condensed water from bottom to top, and stir the reaction at 25°C. 4h to obtain a reaction solution containing 2-nitro-4-fluoroacetanilide compound; further, the speed of the stirring reaction is 500 revolutions/min.This example also includes further purification of the 2-nitro-4-fluoroacetanilide compound: pour the reaction solution containing the 2-nitro-4-fluoroacetanilide compound into a separatory funnel, add 15 mL of distilled water, add 10 mL of ethyl acetate The ester was extracted three times, and the organic phase was distilled under reduced pressure to obtain a crude product, which was separated and purified by column chromatography to obtain a 2-nitro-4-fluoroacetanilide compound with a yield of 58%.
56%	With HNO₃ In sulfuric acid at 0 - 5℃;
	With HNO₃; acetic anhydride; glacial acetic acid
	With sulfuric acid; HNO₃
	(nitration);
	With sulfuric acid; HNO₃ at 0 - 3℃;
	With sulfuric acid; HNO₃ 1.) 0 deg C, 10 min, 2.) RT, 30 min;
	With HNO₃ at 0 - 5℃;
	With HNO₃; acetic anhydride In sulfuric acid	43.A STEP A: STEP A: 2-nitro-4-fluoro-acetanilide 6.5 ml of nitric acid with a density of 1.42 were added at 0° to 5° C. over 30 minutes to a solution of 13.8 g of 4-fluoro-acetanilide [process of Acta Chemica Scand., 1976, p. 141] in 35 ml of concentrated sulfuric acid and the mixture was stirred at 0° to 5° C. for two hours. 10 ml of acetic acid anhydride were added to the mixture which was stirred at 0° C. for one hour and was then poured into ice-water. The mixture was filtered and the solid product was washed and dried to obtain 14 g of 2-nitro-4-fluoro-acetanilide melting at 70°-71° C.
	With HNO₃; acetic anhydride In dichloromethane

Reference： [1]Brindisi, Margherita; Brogi, Simone; Maramai, Samuele; Grillo, Alessandro; Borrelli, Giuseppe; Butini, Stefania; Novellino, Ettore; Allarà, Marco; Ligresti, Alessia; Campiani, Giuseppe; Di Marzo, Vincenzo; Gemma, Sandra [RSC Advances, 2016, vol. 6, # 69, p. 64651 - 64664]
[2]Sana, Sariah; Rajanna; Ali, Mir Moazzam; Saiprakash [Chemistry Letters, 2000, # 1, p. 48 - 49]
[3]Current Patent Assignee: SHANGHAI LINKCHEM TECH - CN112110824, 2020, A Location in patent: Paragraph 0039; 0042; 0046; 0049; 0055; 0058
[4]Gao, Yang; Mao, Yuanyou; Zhang, Biwei; Zhan, Yingying; Huo, Yanping [Organic and Biomolecular Chemistry, 2018, vol. 16, # 21, p. 3881 - 3884]
[5]Current Patent Assignee: HUBEI UNIVERSITY OF TECHNOLOGY - CN113999130, 2022, A Location in patent: Paragraph 0049-0056
[6]Ahmad, Arshad; Dunbar, Linda J.; Green, Iain G.; Harvey, Ian W.; Shepherd, Thomas; et al. [Journal of the Chemical Society. Perkin transactions I, 1994, # 19, p. 2751 - 2758]
[7]Clark; Pessolano [Journal of the American Chemical Society, 1958, vol. 80, p. 1662]
[8]Ghosh; Ternai; Whitehouse [Journal of medicinal chemistry, 1972, vol. 15, # 3, p. 255 - 260]
[9]Liedholm,B. [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1976, vol. 30, p. 141 - 149]
[10]Pujari, H. K.; Sharma, B. R.; Dahiya, Rajender; Kumar, Sudhir; Murakami, Yasuoki; Tani, Masanobu [Journal of Fluorine Chemistry, 1990, vol. 46, # 2, p. 343 - 355]
[11]Monge, Antonio; Palop, Juan A.; Cerain, Adela Lopez de; Senador, Virginia; Martinez-Crespo, Francisko J.; et al. [Journal of Medicinal Chemistry, 1995, vol. 38, # 10, p. 1786 - 1792]
[12]Kuhler; Fryklund; Bergman; Weilitz; Lee; Larsson [Journal of Medicinal Chemistry, 1995, vol. 38, # 25, p. 4906 - 4916]
[13]Current Patent Assignee: SANOFI - US4801717, 1989, A
[14]Location in patent: scheme or table Chopra, Sidharth; Koolpe, Gary A.; Tambo-Ong, Arlyn A.; Matsuyama, Karen N.; Ryan, Kenneth J.; Tran, Tran B.; Doppalapudi, Rupa S.; Riccio, Edward S.; Iyer, Lalitha V.; Green, Carol E.; Wan, Baojie; Franzblau, Scott G.; Madrid, Peter B. [Journal of Medicinal Chemistry, 2012, vol. 55, # 13, p. 6047 - 6060]

5
[ 351-83-7 ]
[ 38962-61-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With sulfuric acid at 60 - 65℃; for 4h;
	With sulfuric acid at 145℃;

Reference： [1]Courtin, Alfred [Helvetica Chimica Acta, 1982, vol. 65, # 2, p. 546 - 550]
[2]Suter; Weston [Journal of the American Chemical Society, 1940, vol. 62, p. 604]

6
[ 108-24-7 ]
[ 371-40-4 ]
[ 351-83-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	In dichloromethane at 20℃; Inert atmosphere;
99.4%	In toluene at 5 - 25℃; for 2h; Large scale;	1.1; 2.1; 3.1 Step 1: Add toluene (3L) into the reactor, and then add 4-fluoroaniline (1.5kg). The ice water is cooled to 5-15°C, and acetic anhydride (1.34kg) is added dropwise for about 2 hours. During the dropping, the temperature is 10-25 °C and the temperature is kept at 20-25°C for 2 hours. Add 4L of water, stir for 30 minutes, filter with suction, rinse the solid with 2L of water, and dry at 50°C to obtain 2046.0g of 4-fluoroacetanilide, yield 99.4%;
99%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 1h;	N-(4-fluorophenyl)acetamide (8). To a solution of 4-fluoroaniline (1.00 g, 9.00 mmol) andDIPEA (3.14 mL, 18.0 mmol) in DCM (20 mL) was added acetic anhydride (1. mL, 10.8mmol) dropwise at 0 °C. The reaction mixture was stirred at room temperature for 1 h.Then, the reaction was quenched with deionised water (5 mL). After decantation, theaqueous layer was extracted with DCM (3 × 10 mL). The combined organic layers weredried on MgSO4, filtered, and concentrated under vacuum. The residue was purified bycolumn chromatography (Al2O3, cyclohexane/EtOAc, 5/5, v/v) to provide compound 8(1.36 g, 8.88 mmol, 99%) as a white powder. Rf (Al2O3, cyclohexane/EtOAc, 5/5, v/v) 0.41.IR (ATR, cm-1) 3301, 3271, 1662, 1618, 1556, 1503, 1204, 831. Mp 153 ± 1 °C (Lit. mp 152-153 °C [39]). 1H NMR (500 MHz, CDCl3) δ 7.89 (br.s, 1H, NH), 7.44 (dd, 2H, 3JH-H = 9.0 Hz,4JH-F = 4.8 Hz, H-2, H-6), 6.97 (t, 2H, 3JH-H = 3JH-F = 8.7 Hz, H-3, H-5), 2.14 (s, 3H, CH3). 13CNMR (126 MHz, CDCl3) δ 168.43 (1C, CO), 159.53 (d, 1C, 1JC-F = 244 Hz, C-4), 133.97 (1C,4JC-F = 3 Hz, C-1), 121.92 (d, 2C, 3JC-F = 8 Hz, C-2, C-6), 115.77 (d, 2C, 2JC-F = 22 Hz, C-3, C-5),24.56 (1C, CH3). 19F NMR (470 MHz, CDCl3) δ-118.97.

97%
97%	In dichloromethane at 20℃; for 0.25h;	3.1. N-Phenylacetamide (11a) General procedure: To aniline (7a, 930mg, 10mmol) dissolved in DCM (10ml), acetic anhydride (1122mg, 11mmol) was added while cooling. After addition the reaction mixture was stirred at room temperature for 15 min. After completion of the reaction water was added and the compound was extracted using DCM. The solvent was evaporated under reduced pressure to afford compound 11a in excellent yield (98%).
96%	With 1,8-diazabicyclo[5.4.0]undec-7-en-8-ium acetate In neat (no solvent) at 50℃; for 0.5h; Green chemistry;
96%	With glacial acetic acid at 20℃; for 0.5h;
92%	With pentaaminechlorocobalt(III) dichloride; phosphoric acid In neat (no solvent) at 75℃; for 0.166667h; Green chemistry; chemoselective reaction;
89%	With N,N'-dimethyl-N,N'-di(pyridin-4-yl)ferrocene-1,1'-dicarboxamide at 20℃; for 0.583333h;
83%	In dichloromethane at 20℃; Inert atmosphere;
42%	at 20℃; for 2h;
	In glacial acetic acid for 0.25h; Heating;
	at 110℃; for 2h;
	With hydrogenchloride at 90℃;
		9.a Acetic anhydride (2.76 g, 27 mmol) was added dropwise to 4-fluoroaniline (3.0 g, 27 mmol) under an atmosphere of nitrogen. The mixture solidified during the addition. 1- Bromo-4-fluorobenzene (4.78 g, 27 mmol) was added to the mixture. Potassium carbonate (5.3 g, 38 mmol) and copper iodide (500 mg) was added and the mixture was heated to 240 0C and the mixture was stirred for 4 h. The mixture was diluted first with xylene and then, after cooling to room temperature, with DCM. The organic layers were combined and the EPO solvent was removed. Purification on silica gel eluting with DCM:MeOH (99:1- > 9:1) gave 3.0 g (46% yield) of the title compound.
	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;
	at 20℃; for 0.5h;
	With glacial acetic acid at 50℃; for 3h;
	With platinum nanoparticles supported on zirconia In methanol at 20℃; for 0.5h;
	With triethylamine In dichloromethane
	With glacial acetic acid Reflux;
	In dichloromethane at 20℃; Inert atmosphere;
	In dichloromethane at 20℃;
	With glacial acetic acid for 0.5h; Heating;
	With pyridine for 0.0833333h;	Derivatization General procedure: For the preparation of the acetyl derivatives, each amine was treated with a mixture (1 mL) of acetic anhydride (95%) and pyridine (5%). After 5 min, the reaction mixture was acidified with 1 M HCl (0.75 mL), and extracted into dichloromethane (1 mL). The extracts were then dried with a stream of N2 to obtain the products as solids or oily residues.
	In dichloromethane at 20℃; Inert atmosphere;	Anilides 1;17 General Procedure General procedure: Arylamine (10.0 mmol; 1 equiv) was added to a round-bottom flask and fitted with a rubber septum. The flask was purged with N2 and anhyd CH2Cl2 (3 mL/1 mmol) was added. Ac2O (12.0 mmol, 1.2 equiv) was added and the reaction was stirred at r.t. and monitored by TLC. Upon completion, the reaction mixture was washed with a sat. aq Na2CO3, the organic layer was dried (MgSO4), and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography using EtOAc/n-hexane as eluent.
	In glacial acetic acid for 1h; Reflux;
	In dichloromethane at 0 - 20℃; Inert atmosphere;
	In dichloromethane at 0℃; for 0.333333h; Inert atmosphere; Schlenk technique;
	In dichloromethane at 0 - 20℃; Inert atmosphere;
	With glacial acetic acid for 1h; Reflux;
	In lithium hydroxide monohydrate
	In tetrahydrofuran at 20℃;
	at 20℃;	General procedure for the preparation of acetanilide derivatives General procedure: To a mixture of aniline (2.0 mmol) was added acetic anhydride (6.0 mmol) and the reaction mixture was stirred at room temperature. The progress of the reaction was monitored by TLC. After the completion of the reaction, CH2Cl2 (20 mL) was added to the mixture. Then the organic solvent was washed with H2O (3×10 mL) and a saturated solution of NaHCO3 (20 mL) and dried over anhydrous Na2SO4. After removal of the solvent, the pure product was obtained.
1635 kg	In dichloromethane at 25℃; Large scale;	1.3; 2.3 (3) 900kg of methylene chloride was added to the reaction kettle, 300kg of compound B was added, 400kg of acetic anhydride was added dropwise, the temperature was controlled at 25°C, and the temperature was kept at 25°C after the dropwise addition, and 1635kg of compound C was obtained.

Reference： [1]Patel, Pitambar; Borah, Gongutri [Chemical Communications, 2017, vol. 53, # 2, p. 443 - 446]
[2]Current Patent Assignee: SHANGHAI LINKCHEM TECH - CN112110824, 2020, A Location in patent: Paragraph 0039; 0041; 0046; 0048; 0055; 0057
[3]Arnaud, Lucie; Chezal, Jean-Michel; Deuther-Conrad, Winnie; Dukic-Stefanovic, Sladjana; Kopka, Klaus; Lai, Thu-Hang; Maisonial-Besset, Aurélie; Miot-Noirault, Elisabeth; Roux, Valérie; Teodoro, Rodrigo; Weber, Valérie; Wenzel, Barbara [Molecules, 2022, vol. 27, # 12]
[4]Zakrzewska; Kolehmainen; Osmialowski; Gawinecki [Journal of Fluorine Chemistry, 2001, vol. 111, # 1, p. 1 - 10]
[5]Shaik, Thokhir B.; Hussaini, S.M. Ali; Nayak, V. Lakshma; Sucharitha, M. Lakshmi; Malik, M. Shaheer; Kamal, Ahmed [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 11, p. 2549 - 2558]
[6]Ji, Li; Qian, Chao; Chen, Xin-Zhi [Monatshefte fur Chemie, 2013, vol. 144, # 3, p. 369 - 374]
[7]Bokosi, Fostino R. B.; Beteck, Richard M.; Jordaan, Audrey; Seldon, Ronnet; Warner, Digby F.; Tshiwawa, Tendamudzimu; Lobb, Kevin; Khanye, Setshaba D. [Journal of Heterocyclic Chemistry, 2021, vol. 58, # 11, p. 2140 - 2151]
[8]Sarief, Abdulla; Haque, SK Manirul; Feroze, Syed Mudabbir; Arifuddin, Mohammed [Journal of the Chinese Chemical Society, 2018, vol. 65, # 9, p. 1104 - 1109]
[9]Kashyap, Bishwapran; Phukan, Prodeep [RSC Advances, 2013, vol. 3, # 35, p. 15327 - 15336]
[10]Stuart, David R.; Bertrand-Laperle, Megan; Burgess, Kevin M. N.; Fagnou, Keith [Journal of the American Chemical Society, 2008, vol. 130, # 49, p. 16474 - 16475]
[11]Linstad, Ethan J.; Vāvere, Amy L.; Hu, Bao; Kempinger, Jayson J.; Snyder, Scott E.; DiMagno, Stephen G. [Organic and Biomolecular Chemistry, 2017, vol. 15, # 10, p. 2246 - 2252]
[12]Wallach; Heusler [Justus Liebigs Annalen der Chemie, 1888, vol. 243, p. 223] Holleman,A.F. [Recueil des Travaux Chimiques des Pays-Bas, 1906, vol. 25, p. 330] Suter; Weston [Journal of the American Chemical Society, 1940, vol. 62, p. 604] Forsyth, David A.; Yang, Jun-Rui [Journal of the American Chemical Society, 1986, vol. 108, # 9, p. 2157 - 2161] Hansen, Poul Erik; Bolvig, Simon; Buvari-Barcza, Agnes; Lycka, Antonin [Acta Chemica Scandinavica, 1997, vol. 51, # 8, p. 881 - 888]
[13]Monge, Antonio; Palop, Juan A.; Cerain, Adela Lopez de; Senador, Virginia; Martinez-Crespo, Francisko J.; et al. [Journal of Medicinal Chemistry, 1995, vol. 38, # 10, p. 1786 - 1792]
[14]Kuhler; Fryklund; Bergman; Weilitz; Lee; Larsson [Journal of Medicinal Chemistry, 1995, vol. 38, # 25, p. 4906 - 4916]
[15]Leyva, Socorro; Castanedo, Víctor; Leyva, Elisa [Journal of Fluorine Chemistry, 2003, vol. 121, # 2, p. 171 - 175]
[16]Current Patent Assignee: ASTRAZENECA PLC - WO2006/68594, 2006, A1 Location in patent: Page/Page column 51-52
[17]Location in patent: experimental part Shah, Neel H.; Butterfoss, Glenn L.; Nguyen, Khanh; Yoo, Barney; Bonneau, Richard; Rabenstein, Dallas L.; Kirshenbaum, Kent [Journal of the American Chemical Society, 2008, vol. 130, # 49, p. 16622 - 16632]
[18]Location in patent: experimental part Kantam, M. Lakshmi; Reddy, R. Sudarshan; Srinivas; Chakravarti; Sreedhar; Figueras; Venkat Reddy, Ch. [Journal of Molecular Catalysis A: Chemical, 2012, vol. 355, p. 96 - 101]
[19]Location in patent: experimental part Wang, Yunchun; Bai, Zhongyuan; Wei, Zengjun; Xu, Shengzhen; Li, Xuegang; Li, Jianhong; Cao, Xiufang; Chen, Changshui [Research on Chemical Intermediates, 2011, vol. 37, # 8, p. 1029 - 1039]
[20]Location in patent: scheme or table Kantam, M. Lakshmi; Reddy, R. Sudarshan; Srinivas; Chakravarti; Sreedhar; Figueras; Reddy, Ch. Venkat [Journal of Molecular Catalysis A: Chemical, 2012, vol. 357, p. 175 - 176]
[21]Location in patent: scheme or table Chopra, Sidharth; Koolpe, Gary A.; Tambo-Ong, Arlyn A.; Matsuyama, Karen N.; Ryan, Kenneth J.; Tran, Tran B.; Doppalapudi, Rupa S.; Riccio, Edward S.; Iyer, Lalitha V.; Green, Carol E.; Wan, Baojie; Franzblau, Scott G.; Madrid, Peter B. [Journal of Medicinal Chemistry, 2012, vol. 55, # 13, p. 6047 - 6060]
[22]Fernández-Galleguillos, Carlos; Saavedra, Luis A.; Gutierrez, Margarita [Journal of the Brazilian Chemical Society, 2014, vol. 25, # 2, p. 365 - 371]
[23]Gao, Yang; Huang, Yubing; Wu, Wanqing; Huang, Kefan; Jiang, Huanfeng [Chemical Communications, 2014, vol. 50, # 61, p. 8370 - 8373] Kathiravan, Subban; Nicholls, Ian A. [Chemistry - A European Journal, 2017, vol. 23, # 29, p. 7031 - 7036]
[24]Luo, Feihua; Yang, Jun; Li, Zhengkai; Xiang, Haifeng; Zhou, Xiangge [European Journal of Organic Chemistry, 2015, vol. 2015, # 11, p. 2463 - 2469]
[25]Raghavan, Saiharish; Manogaran, Prasath; Gadepalli Narasimha, Krishna Kumari; Kalpattu Kuppusami, Balasubramanian; Mariyappan, Palanivelu; Gopalakrishnan, Anjana; Venkatraman, Ganesh [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 17, p. 3601 - 3605]
[26]Hassan, Isra; Pinto, Spencer; Weisbecker, Carl; Attygalle, Athula B. [Journal of the American Society for Mass Spectrometry, 2016, vol. 27, # 3, p. 394 - 401]
[27]Gandeepan, Parthasarathy; Rajamalli, Pachaiyappan; Cheng, Chien-Hong [Synthesis, 2016, vol. 48, # 12, p. 1872 - 1879]
[28]Govender, Hogantharanni; Mocktar, Chunderika; Koorbanally, Neil A. [Journal of Heterocyclic Chemistry, 2018, vol. 55, # 4, p. 1002 - 1009]
[29]Gao, Yang; Mao, Yuanyou; Zhang, Biwei; Zhan, Yingying; Huo, Yanping [Organic and Biomolecular Chemistry, 2018, vol. 16, # 21, p. 3881 - 3884]
[30]Wang, Na; Gu, Qiang-Shuai; Li, Zhong-Liang; Li, Zhuang; Guo, Yu-Long; Guo, Zhen; Liu, Xin-Yuan [Angewandte Chemie - International Edition, 2018, vol. 57, # 43, p. 14225 - 14229][Angew. Chem., 2018, vol. 130, # 43, p. 14421 - 14425,5]
[31]Ghosh, Chiranjit; Nagtilak, Prajyot Jayadev; Kapur, Manmohan [Organic Letters, 2019]
[32]Govender, Hogantharanni; Mocktar, Chunderika; Kumalo, Hezekiel M.; Koorbanally, Neil A. [Phosphorus, Sulfur and Silicon and the Related Elements, 2019, vol. 194, # 11, p. 1074 - 1081]
[33]Chakraborty, Subhayan; Peruncheralathan; Ghosh, Arindam [RSC Advances, 2021, vol. 11, # 12, p. 6526 - 6534]
[34]Kumar, Vasantha; Rai, Vaishali M.; Udupi, Vishwanatha; Shivalingegowda, Naveen; Pai, Vinitha R.; Krishnappagowda, Lokanath Neratur; Poojary, Boja [Journal of the Iranian Chemical Society, 2022, vol. 19, # 3, p. 793 - 808]
[35]Kianmehr, Ebrahim; Doraghi, Fatemeh; Foroumadi, Alireza [Synthesis, 2022, vol. 54, # 10, p. 2464 - 2472]
[36]Current Patent Assignee: NINGXIA GINSENG PHARMACEUTICAL INDUSTRY LTD - CN114163346, 2022, A Location in patent: Paragraph 0009; 0011

7
[ 1795-83-1 ]
[ 351-83-7 ]

Yield	Reaction Conditions	Operation in experiment
71%	With diethylamino-sulfur trifluoride In dichloromethane at 0℃; for 0.0833333h;
142 g	With potassium fluoride; fluorosulfonyl fluoride In dichloromethane at 0 - 20℃; for 12h; Sealed tube;	1 Example 1 Add N-acetylphenylhydroxylamine (151g, 1.0mol), KF (29g, 0.5mol) and dichloromethane (1.0L) in sequence to a stirred 2L reaction flask, cool to 0°C, and pour in sulfonyl fluoride (202g, 2mol), seal the system, slowly warm to room temperature, stir and react for 12h, add saturated brine (500mL) to wash after the reaction, and concentrate the organic phase under reduced pressure to distill off dichloromethane (recycling). The crude product is refined under reduced pressure. Distillation to obtain white solid N-acetyl 4-fluoroaniline (142g), add N-acetyl 4-fluoroaniline to 2mol/L hydrochloric acid (500mL), heat to reflux for 12h, TLC detects the completion of the reaction, add Adjust the pH to alkaline (8-10) with NaOH (5mol/L), add organic solvent dichloromethane (500mL) for extraction, wash the organic phase with saturated brine, dry with anhydrous sodium sulfate, and distill under reduced pressure to recover the solvent. Under reduced pressure distillation, pure 4-fluoroaniline was obtained as a pale yellow liquid (101 g, yield 91%, purity 99.3%).

Reference： [1]Kikugawa, Yasuo; Matsumoto, Kazuhiro; Mitsui, Kimiyo; Sakamoto, Takeshi [Journal of the Chemical Society. Chemical communications, 1992, # 12, p. 921 - 922]
[2]Current Patent Assignee: JIANGSU DUXING ZHIYUAN NEW MATERIAL TECH - CN113416139, 2021, A Location in patent: Paragraph 0045-0047

8
[ 16375-88-5 ]
[ 351-83-7 ]

Reference： [1]Journal of Fluorine Chemistry,1991,vol. 54,p. 268

9
[ 103-84-4 ]
[ 351-83-7 ]
[ 399-31-5 ]

Yield	Reaction Conditions	Operation in experiment
1: 74.5% 2: 11%	With cesium fluoroxysulphate; boron trifluoride In acetonitrile for 0.5h; Ambient temperature;
1: 20% 2: 58%	With Selectfluor In nitromethane at 50℃; for 24h;
1: 55% 2: 8%	With acetyl hypofluorite In dichloromethane; trichlorofluoromethane at -75℃;

1: 46% 2: 26%	With Selectfluor In nitromethane; water at 50℃; for 24h;
1: 28% 2: 23%	With N-Fluoro-2,6-bis(methoxycarbonyl)pyridinium triflate In dichloromethane for 48h; Heating;
	With acetyl hypofluorite; sodium acetate In trichlorofluoromethane; acetic acid at -75℃; Yield given. Yields of byproduct given;
	With Selectfluor In acetonitrile for 0.25h; Heating; Yield given. Yields of byproduct given;
	With acetyl hypofluorite In acetic acid for 0.0833333h; Ambient temperature; Yield given. Yields of byproduct given;
	With 1-fluoro-4-methyl-1,4-diazoniabicyclo<2.2.2>octane ditriflate In methanol Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	With 1-fluoro-4-methyl-1,4-diazoniabicyclo<2.2.2>octane ditriflate In methanol Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	With 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2,2,2]octane-1,4-bis(tetrafluoroborate) In acetonitrile at 40℃; for 6h; Title compound not separated from byproducts;

Reference： [1]Stavber, Stojan; Zupan, Marko [Journal of Organic Chemistry, 1985, vol. 50, # 19, p. 3609 - 3612]
[2]Liang, Deqiang; Li, Yanni; Gao, Shulin; Li, Renlun; Li, Xiangguang; Wang, Baoling; Yang, Hai [Green Chemistry, 2017, vol. 19, # 14, p. 3344 - 3349]
[3]Lerman, Ori; Yitzhak, Tor; Hebel, David; Rozen, Shlomo [Journal of Organic Chemistry, 1984, vol. 49, p. 806 - 813]
[4]Liang, Deqiang; Li, Yanni; Gao, Shulin; Li, Renlun; Li, Xiangguang; Wang, Baoling; Yang, Hai [Green Chemistry, 2017, vol. 19, # 14, p. 3344 - 3349]
[5]Umemoto, Teruo; Fukami, Shinji; Tomizawa, Ginjiro; Harasawa, Kikuko; Kawada, Kosuke; Tomita, Kyoichi [Journal of the American Chemical Society, 1990, vol. 112, # 23, p. 8563 - 8575]
[6]Lerman, Ori; Tor, Yitzhak; Rozen, Shlomo [Journal of Organic Chemistry, 1981, vol. 46, # 22, p. 4629 - 4631]
[7]Banks, R. Eric; Mohialdin-Khaffaf, Suad N.; Lai, G. Sankar; Sharif, Iqbal; Syvret, Robert G. [Journal of the Chemical Society. Chemical communications, 1992, # 8, p. 595 - 596]
[8]Visser, Gerard W. M.; Halteren, Bert W. v.; Herscheid, Jacobus D. M.; Brinkman, Gerard A.; Hoekstra, Arend [Journal of the Chemical Society. Chemical communications, 1984, # 10, p. 655 - 656]
[9]Banks, R. Eric; Besheesh, Mohamed K.; Mohialdin-Khaffaf, Suad N.; Sharif, Iqbal [Journal of the Chemical Society. Perkin transactions I, 1996, # 16, p. 2069 - 2076]
[10]Banks, R. Eric; Besheesh, Mohamed K.; Mohialdin-Khaffaf, Suad N.; Sharif, Iqbal [Journal of the Chemical Society. Perkin transactions I, 1996, # 16, p. 2069 - 2076]
[11]Poss, Andrew J.; Shia, George A. [Tetrahedron Letters, 1999, vol. 40, # 14, p. 2673 - 2676]

10
[ 103-84-4 ]
[ 351-83-7 ]
[ 399-31-5 ]
[ 399-36-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 16% 2: 6% 3: 58%	With 2,3,4,5,6-pentachloro-1-fluoropyridin-1-ium trifluoromethanesulfonate In dichloromethane at 0 - 20℃; for 23h;
1: 58% 2: 16% 3: 6%	With 2,3,4,5,6-pentachloro-1-fluoropyridin-1-ium trifluoromethanesulfonate In dichloromethane at 0 - 20℃; for 23h;

Reference： [1]Umemoto, Teruo; Fukami, Shinji; Tomizawa, Ginjiro; Harasawa, Kikuko; Kawada, Kosuke; Tomita, Kyoichi [Journal of the American Chemical Society, 1990, vol. 112, # 23, p. 8563 - 8575]
[2]Umemoto, Teruo; Fukami, Shinji; Tomizawa, Ginjiro; Harasawa, Kikuko; Kawada, Kosuke; Tomita, Kyoichi [Journal of the American Chemical Society, 1990, vol. 112, # 23, p. 8563 - 8575]

11
[ 371-40-4 ]
[ 4232-27-3 ]
[ 351-83-7 ]
[ 20350-26-9 ]

Reference： [1]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1990,vol. 29,p. 757 - 760

12
[ 351-83-7 ]
[ 33513-42-7 ]
[ 749920-54-5 ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0 - 5℃; for 1h; Stage #2: N₁-(4-Fluorophenyl)acetamide at 0 - 80℃; Inert atmosphere;	1.1 General procedure for synthesis of 2-chloroquinoline-3-carbaldehydes (13-18) General procedure: A round bottom flask charged with N, N-dimethylformamide (7.0 mol) was placed on an ice bath and the temperature kept at 0-5 °C. To this flask, phosphorus oxychloride (12.0 mol) was added dropwise and the reaction mixture was stirred for 1 h at 0-5 °C. The appropriate N-phenylacetamide (1.0 mol) was then added and stirred for a further 30 min followed by heating under reflux for 5-4 h under N2 atmosphere. After the reaction was completed (TLC monitoring), the mixture was poured into 200 g of crushed ice under constant stirring. The precipitate obtained was vacuum filtered, washed with water (2 × 30 mL), air-dried and recrystallised from EtOAc to give the relevant compounds in 36-84% yields.
55%	Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0 - 5℃; for 1h; Inert atmosphere; Stage #2: N₁-(4-Fluorophenyl)acetamide at 0℃; Inert atmosphere; Reflux;
40%	With trichlorophosphate at 85℃; for 24h;

15%	With trichlorophosphate at 0 - 82℃;	36a; 36b 2-Chloro-6-fluoroquinoline-3-carbaldehyde To DMF (18.94 mL, 18.94 mL) at 0° C. was added POCl3 (63.90 mL, 685.6 mmol) dropwise, then N-(4-fluorophenyl)acetamide (15.00 g, 97.94 mmol) portionwise. The mixture was stirred at 0° C. for 20 min, then at 82° C. overnight. The mixture was allowed to cool to RT then poured into ice-water. Precipitate was collected by filtration and and dried to give the title compound as a yellow solid (3.16 g, 15%). MS (ES+): C10H5ClFNO requires: 209, found: 210 [M+H]+.
13%	Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0 - 20℃; for 0.25h; Inert atmosphere; Stage #2: N₁-(4-Fluorophenyl)acetamide In dichloromethane at 85℃; for 19h; Inert atmosphere;	2-chloro-3-formyl-6-fluoroquinoline (10). Under anhydrous argon atmosphere, POCl3(4.2 mL, 45.7 mmol) was added dropwise to precooled (0 °C) anhydrous DMF (1.25 mL,16.3 mmol). The solution was allowed to warm to room temperature (15 min) and thentreated with compound 8 (1.00 g, 6.53 mmol). The round-bottom flask was sealed, and thesolution was stirred at 85 °C for 19 h. After cooling to room temperature, the solution wasthen poured over ice (100 mL). The yellow precipitate was filtered, washed with deionisedwater (20 mL), and dried under vacuum to provide compound 10 (182 mg, 0.868 mmol,13%) as a yellow powder. Rf (SiO2, cyclohexane/EtOAc, 9/1, v/v) 0.40. IR (ATR, cm-1) 1693(νC=O), 1581, 1497 (νC=C), 1337 (νC-N), 1220 (νC-F), 1046 (νS=O), 834 (δCH op). Mp 180 ± 1 °C. 1HNMR (500 MHz, CDCl3) δ 10.38 (s, 1H, CHO), 8.97 (s, 1H, H-4), 8.15-8.10 (m, 2H, H-5, H-7), 7.92 (td, 1H, 3JH-H = 3JH-F = 8.7 Hz, 4JH-H = 3.0 Hz, H-7). 13C NMR (126 MHz, CDCl3) δ 189.08(1C, CHO), 161.21 (d, 1C, 1JC-F = 250 Hz, C-6), 149.60 (d, 1C, 4JC-F = 3 Hz, C-8a), 146.82 (1C,C-2 or C-3), 139.65 (d, 1C, 4JC-F = 6Hz, C-4), 131.34 (d, 1C, 3JC-F = 9 Hz, C-8), 127.49 (d, 1C, 3JCF= 10 Hz, C-4a), 127.05 (1C, C-2 or C-3), 123.98 (d, 1C, 2JC-F = 26 Hz, C-7), 112.80 (d, 1C, 2JCF= 22 Hz, C-5). 19F NMR (470 MHz, CDCl3) δ-110.89. HRMS (ESI) m/z 210.0113 [M+H]+(calculated for [C11H6ClFNO]+ 210,0116), 242.0375 [M+32] (calculated for [C11H10ClFNO2]+242.0384, methyl hemiacetal form).
	With trichlorophosphate 1.) 0 deg C, 0.5 h, 2.) 70 deg C, 16 h; Multistep reaction;
	With trichlorophosphate
	With trichlorophosphate Heating;
	With trichlorophosphate at 0 - 82℃; for 24h; Inert atmosphere;
	With trichlorophosphate at 75℃; for 8h;	4.2. General procedure for the synthesis of compounds 2a-2f General procedure: POCl3 (9.0 mL, 96 mmol) was added dropwise to DMF (2.8 mL,36 mmol) precooled at 0 C. Followed by adding acetanilide(10 mmol), the mixture was heated to 75 °C and stirred at thattemperature for 8 h. After been cooled to room temperature, themixture was poured to 100mL of ice-water. The precipitate wasobtained by suction filtration, washed with cold water and dried toafford the product.1H NMR and 13C NMR data of selected productsare shown as follows.
	With trichlorophosphate for 24h; Heating;
	Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 0.25h; Stage #2: N₁-(4-Fluorophenyl)acetamide at 80℃; for 8h;
	With trichlorophosphate for 6h; Reflux;

Reference： [1]Bokosi, Fostino R.B.; Beteck, Richard M.; Mbaba, Mziyanda; Mtshare, Thanduxolo E.; Laming, Dustin; Hoppe, Heinrich C.; Khanye, Setshaba D. [Bioorganic and Medicinal Chemistry Letters, 2021, vol. 38]
[2]Bokosi, Fostino R. B.; Beteck, Richard M.; Jordaan, Audrey; Seldon, Ronnet; Warner, Digby F.; Tshiwawa, Tendamudzimu; Lobb, Kevin; Khanye, Setshaba D. [Journal of Heterocyclic Chemistry, 2021, vol. 58, # 11, p. 2140 - 2151]
[3]Fernández-Galleguillos, Carlos; Saavedra, Luis A.; Gutierrez, Margarita [Journal of the Brazilian Chemical Society, 2014, vol. 25, # 2, p. 365 - 371]
[4]Current Patent Assignee: THE UNIVERSITY OF TEXAS SYSTEM - US2019/308978, 2019, A1 Location in patent: Paragraph 0849; 0850
[5]Arnaud, Lucie; Chezal, Jean-Michel; Deuther-Conrad, Winnie; Dukic-Stefanovic, Sladjana; Kopka, Klaus; Lai, Thu-Hang; Maisonial-Besset, Aurélie; Miot-Noirault, Elisabeth; Roux, Valérie; Teodoro, Rodrigo; Weber, Valérie; Wenzel, Barbara [Molecules, 2022, vol. 27, # 12]
[6]Lavergne, Olivier; Lesueur-Ginot, Laurence; Rodas, Francesc Pla; Kasprzyk, Philip G.; Pommier, Jacques; Demarquay, Danièle; Prévost, Grégoire; Ulibarri, Gérard; Rolland, Alain; Schiano-Liberatore, Anne-Marie; Harnett, Jeremiah; Pons, Dominique; Camara, José; Bigg, Dennis C. H. [Journal of Medicinal Chemistry, 1998, vol. 41, # 27, p. 5410 - 5419]
[7]Khunt, Ranjan C.; Khedkar, Vijay M.; Coutinho, Evans C. [Chemical Biology and Drug Design, 2013, vol. 82, # 6, p. 669 - 684]
[8]Raghavan, Saiharish; Manogaran, Prasath; Gadepalli Narasimha, Krishna Kumari; Kalpattu Kuppusami, Balasubramanian; Mariyappan, Palanivelu; Gopalakrishnan, Anjana; Venkatraman, Ganesh [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 17, p. 3601 - 3605]
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[10]Zhao, Yan; Li, Min; Li, Bowen; Zhang, Shun; Su, Aoze; Xing, Yongning; Ge, Zemei; Li, Runtao; Yang, Baoxue [European Journal of Medicinal Chemistry, 2019, vol. 172, p. 131 - 142]
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13
[ 329-79-3 ]
[ 351-83-7 ]

Yield	Reaction Conditions	Operation in experiment
97%	With 2,2-dichloro-1,3-dicyclohexylimidazolidine-4,5-dione In acetonitrile at 80℃; for 0.166667h; Schlenk technique; Inert atmosphere; Green chemistry;	11 In a sealed Schlenk tube, 2,2-dichloro-1,3-dicyclohexylimidazolidine-4,5-dione (7) (33.33mg, 0. Lmmol), p-fluoroacetophenone oxime (0.153g, lmmol) dissolved in 10mL acetonitrile, under the control of Ar heating and heating to 80 ° C, for 10min raw material completely transformed, the target product of fluorine Aniline selectivity of 99%. After completion of the reaction, the solvent was distilled off under reduced pressure and purified by flash chromatography to give pure p-fluoroacetanilide as a pale yellow solid, The yield was 97%.
96%	Stage #1: 1-(4-fluorophenyl)ethanone oxime With fluorosulfonyl fluoride; triethylamine In acetonitrile at 20℃; Stage #2: With hydrogenchloride In water; acetonitrile at 20℃;
94%	With ethyl 2-cyano-2-(2-nitrobenzenesulfonyloxyimino)acetate In acetonitrile at 85℃; Microwave irradiation; Inert atmosphere;

92%	With trifluoromethylsulfonic anhydride In dichloromethane at 20℃; for 3.5h; Inert atmosphere;
92%	With 1,1,1,3',3',3'-hexafluoro-propanol; perfluoropinacol; 2-(phenoxycarbonyl)phenylboronic acid In nitromethane at 20℃; for 24h; chemoselective reaction;
90%	With oxalyl dichloride at 0 - 20℃; for 2h;	4.2 Typical procedure for synthesis of compound 2a General procedure: Polystyrene-supported phosphine oxide (10.4 mg, 2.5 mol%), (E)-1-Phenylethan-1-one oxime 1a (67.5 mg, 0.5 mmol) and HFIP (2 mL) were added to a 10-mL glass vessel containing a magnetic stirring bar. Then, oxalyl chloride (64.8 mg, 0.5 mmol) was added at 0 °C. The mixture was stirred at room temperature for 2 h. After completion of the reaction (indicated by TLC), the catalyst was removed by filtration and the solvent was removed under reduced pressure. The crude material was purified by silica gel column using PE/EtOAc as the eluent to afford the desired product 2a in 99% yield.
89%	With 1-methylimidazole hydrogen sulfate; phosphorus pentoxide In neat (no solvent) at 90℃; for 6h; Inert atmosphere;	3.3. 1.1. General Procedures for the Synthesis of Amides 3a-3o General procedure: To a solution of the oxime substrates 2a-2o (9.50 mmol) in (HMIm)HSO4 (2.05 g, 11.4 mmol), the co-catalyst P2O5 (0.15 g, 1.0 mmol) was added. Then the solution was heated to 90 °C and the reaction was monitored by TLC. After completion of the reaction, the mixture was extracted with ethyl acetate (50 mL) twice, and the combined organic phase was washed with the aqueous solution of sodium bicarbonate and brine, dried over anhydrous Na2SO4 and concentrated in vacuo to afford a residue, which was purifi ed by column (ethylacetate: petroleum ether = 1:4) to afford the products 3a-3o. 3a [22]: White solid, Yield: 91%. m.p.: 127.0-128.0 C; 1H-NMR (600 MHz, DMSO-d6) δ 9.80 (brs, 1H), 7.51-7.46 (m, 2H), 7.20 (d, J = 7.9 Hz, 1H), 6.89-6.84 (m, 2H), 3.71 (s, 3H), 2.01 (s, 3H); 13C-NMR (150 MHz, DMSO-d6) δ 168.2, 155.5, 133.0, 121.0, 114.2, 55.6, 24.3; HRMS(+): calcd. for C9H11NO2 [M + H]+ 166.0863, found 166.0859; calcd. for C9H11NO2Na [M + Na]+ 188.0682, found 188.0682.
86%	With dimethylbromosulphonium bromide at 80℃; for 3h; Ionic liquid;
86%	With dimethylbromosulphonium bromide; zinc(II) chloride In acetonitrile for 3h; Reflux;
79%	With carbon tetrabromide; triphenylphosphine In toluene at 80℃; for 1h; Inert atmosphere;
77%	With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine In water; acetonitrile at 20℃; for 2h;
75%	With ammonium peroxydisulfate; dimethyl sulfoxide In 1,4-dioxane at 100℃; for 8h; Schlenk technique; Inert atmosphere;
75%	With carbon tetrabromide; N,N-dimethyl-formamide In acetonitrile for 12h; Inert atmosphere; Irradiation; Sealed tube;
74%	With iron(III) chloride; silver hexafluoroantimonate In 1,2-dichloro-ethane at 80℃; for 24h;	Iron-Catalyzed Beckmann Rearragnment; General Procedure General procedure: To an oven-dried 20 mL vial containing FeCl3 (24.3 mg,0.15 equiv), was added a solution of oxime (1 mmol) in DCE (10mL) and the mixture was stirred until FeCl3 was completely dissolved(10-15 min). To this solution was added AgSbF6 (154.6mg, 0.45 equiv), then the vial was capped and put into mechanicalshaker at 80 °C for 24 h. The mixture was filtered throughCelite with CH2Cl2 (100 mL) and concentrated to give a residue,which was purified by silica flash chromatography usinghexanes and ethyl acetate in appropriate combination based onthe Rf of the desired product.
67%	With 10-methyl-9-phenylacridin-10-ium perchlorate In 1,2-dichloro-ethane at 20℃; for 5h; Irradiation; Sealed tube;

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[6]Wang, Yaoyao; Chen, Qun; He, Mingyang; Wang, Liang [Phosphorus, Sulfur and Silicon and the Related Elements, 2019, vol. 194, # 3, p. 210 - 214]
[7]Hu, Hongyu; Cai, Xuting; Xu, Zhuying; Yan, Xiaoyang; Zhao, Shengxian [Molecules, 2018, vol. 23, # 7]
[8]Location in patent: scheme or table Yadav, Lal Dhar S.; Garima; Srivastava, Vishnu P. [Tetrahedron Letters, 2010, vol. 51, # 4, p. 739 - 743]
[9]Location in patent: experimental part Yadav, Lal Dhar S.; Patel, Rajesh; Srivastava, Vishnu P. [Synthesis, 2010, # 11, p. 1771 - 1776]
[10]Gao, Peng; Bai, Zijing [Chinese Journal of Chemistry, 2017, vol. 35, # 11, p. 1673 - 1677]
[11]Isobe, Toshio; Ishikawa, Tsutomu [Journal of Organic Chemistry, 1999, vol. 64, # 16, p. 5832 - 5835]
[12]Mahajan, Pankaj S.; Humne, Vivek T.; Tanpure, Subhash D.; Mhaske, Santosh B. [Organic Letters, 2016, vol. 18, # 14, p. 3450 - 3453]
[13]Zhi, Peng; Xi, Zi-Wei; Wang, Dan-Yan; Wang, Wei; Liang, Xue-Zheng; Tao, Fei-Fei; Shen, Run-Pu; Shen, Yong-Miao [New Journal of Chemistry, 2019, vol. 43, # 2, p. 709 - 717]
[14]Jefferies, Latisha R.; Weber, Savannah R.; Cook, Silas P. [Synlett, 2015, vol. 26, # 3, p. 331 - 334]
[15]Tang, Li; Wang, Zhi-Lv; Wan, Hai-Lan; He, Yan-Hong; Guan, Zhi [Organic Letters, 2020, vol. 22, # 15, p. 6182 - 6186]

14
[ 7664-93-9 ]
[ 351-83-7 ]
[ 38962-61-7 ]

Yield	Reaction Conditions	Operation in experiment
	at 145℃;

Reference： [1]Suter; Weston [Journal of the American Chemical Society, 1940, vol. 62, p. 604]

15
[ 403-42-9 ]
[ 351-83-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With O-benzenesulfonyl-acetohydroxamic acid ethyl ester; toluene-4-sulfonic acid In water; acetonitrile at 23℃; for 24h; Inert atmosphere;
94%	With sodium hydrogen sulfate; hydroxylamine hydrochloride; silica gel for 0.0416667h; Heating;
91%	With O-trifluorobenzenesulfonyl-acetohydroxamic acid ethyl ester; toluene-4-sulfonic acid In water; acetonitrile at 20℃; Inert atmosphere;	1 Example 3 General procedure: Table 2 shows the results of examining various catalysts in the reaction of synthesizing N- (2-naphthyl) acetamide from 2-acetonaphthone. Examples of the acid catalyst include hydrochloric acid, sulfuric acid, methanesulfonic acid, tosylic acid monohydrate, trifluoromethanesulfonic acid, bistrifluoromethanesulfonimide, boron trifluoride diethyl ether complex, scandium (III) trifluoromethanesulfonate, trifluoromethanesulfone Iron (III) oxide, trifluoromethanesulfoCopper (II) trifluoromethanesulfonate, bismuth trifluoromethanesulfonate (III), titanium tetrachloride and iron trichloride have excellent effects (Entries 2 to 14).

85%	With mesitylenesulfonylhydroxylamine In acetonitrile at 20℃; for 10h;	General procedure for the preparation of amides from ketones General procedure: To a round bottom flask, equipped with a magnetic stirring bar, was added ketone 1 (0.5 mmol, 1.0 equiv.) and acetonitrile (2 mL) at room temperature. To this stirred solution, freshly prepared O-(Mesitylsulfonyl)hydroxylamine 2 (2.0 equiv.) was added. The reaction mixture was stirred for the specified duration and temperature. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with ethyl acetate (10 mL) and washed with a saturated aqueous NaHCO3 solution (3 x 5 mL). The combined organic layer was washed with brine solution and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure to get the crude product. The reaction that required elevated temperature was stirred first at room temperature for 2 hours after addition of MSH and then heated at 70 °C for the specified time.
80%	With zinc(II) chloride; hydroxylamine-O-sulfonic acid In water at 80℃; for 9h;	Secondary Amides from Ketones; General Procedure General procedure: To a stirring solution of ZnCl2 (0.05 mmol, 10 mol%) in H2O (2 mL) at r.t. in an open round-bottom flask, ketone 1 (0.5 mmol, 1.0 equiv) wasadded, followed by HOSA (1.5 equiv). The reaction mixture was stirred at the indicated temperature and for the duration indicated in Scheme 2. After completion, the reaction mixture was diluted with EtOAc (15 mL) and washed with sat. aq Na2CO3 (3 × 5 mL). The organic layer was washed with brine (5 mL) and dried over anhydrous Na2SO4.The crude product obtained after removal of all volatiles in vacuo was washed with n-hexane to remove some minor nonpolar impurities.
75%	With nitromethane; trifluoromethylsulfonic anhydride; acetic acid In formic acid at 80 - 120℃;	8 Example 8 p-Fluoroacetanilide Take a reaction tube, add 60-100mg (1.2mmol) of nitromethane, 35-45mg (0.3mmol) of p-fluoroacetophenone, 0.5mL of acetic acid,Trifluoromethanesulfonic anhydride 150-200mg (0.6mmol),30-60 mg (0.75 mmol) of formic acid, stirring at 80-120°C for 1-72 hours. After the completion of the reaction, 10 mL of sodium hydroxide solution was added to quench the reaction, extracted with ethyl acetate 3 times, the organic phase was washed with 5 mL of brine, and the organic phases were combined and separated by column chromatography to obtain 34.4 mg of p-fluoroacetanilide, with a yield of 75%.
75%	With formic acid; nitromethane; trifluoromethylsulfonic anhydride In acetic acid at 100℃; for 12h;
25%	With cesiumhydroxide monohydrate; copper(II) bis(trifluoromethanesulfonate); hydroxylamine-O-sulfonic acid In dichloromethane; 2,2,2-trifluoroethanol at 70℃; for 24h;	Amides from Ketones General procedure: To a stirred solution of Cu(OTf)2 (0.05 mmol, 10 mol%) in TFE/CH2Cl2 (1:4, 2-3 mL) were added ketone (0.5 mmol, 1.0 equiv), HOSA (2.0 equiv), and CsOH·H2O (2.0 equiv) at rt. The reaction mixture was maintained at the temperature and for the time indicated in Scheme 2. After completion, the mixture was diluted with CH2Cl2 (10 mL) and washed with sat. aq Na2CO3 (3 × 5 mL). The combined organic layers were washed with brine (5 mL) and dried (anhyd Na2SO4). The crude product obtained after removal of all volatiles in vacuo was purified by SiO2 (100-200 mesh) chromatography using EtOAc/hexane as eluent.

Reference： [1]Hyodo, Kengo; Hasegawa, Genna; Oishi, Naoki; Kuroda, Kazuma; Uchida, Kingo [Journal of Organic Chemistry, 2018, vol. 83, # 21, p. 13080 - 13087]
[2]Das; Ravindranath; Venkataiah; Madhusudhan [Journal of Chemical Research - Part S, 2000, # 10, p. 482 - 483]
[3]Current Patent Assignee: RYUKOKU UNIVERSITY - JP2018/135293, 2018, A Location in patent: Paragraph 0029; 0031
[4]Chandra, Dinesh; Verma, Saumya; Pandey, Chandra Bhan; Yadav, Ajay K.; Kumar, Puneet; Tiwari, Bhoopendra; Jat, Jawahar L. [Tetrahedron Letters, 2020, vol. 61, # 18]
[5]Verma, Saumya; Kumar, Puneet; Khatana, Anil K.; Chandra, Dinesh; Yadav, Ajay K.; Tiwari, Bhoopendra; Jat, Jawahar L. [Synthesis, 2020, vol. 52, # 21, p. 3272 - 3276]
[6]Current Patent Assignee: PEKING UNIVERSITY - CN112574054, 2021, A Location in patent: Paragraph 0131-0133
[7]Jiao, Ning; Liu, Jianzhong; Qiu, Xu; Song, Song; Wei, Jialiang; Wen, Xiaojin; Zhang, Cheng; Zhang, Ziyao [Science, 2020, vol. 367, # 6475, p. 281 - 285]
[8]Anugu, Raghunath Reddy; Chandra, Dinesh; Falck, John R.; Jat, Jawahar L.; Munnuri, Sailu; Verma, Saumya [Synthesis, 2019, vol. 51, # 19, p. 3709 - 3714]

16
[ 351-83-7 ]
[ 405-67-4 ]

Reference： [1]Chemical Science,2016,vol. 7,p. 3432 - 3442
[2]Advanced Synthesis and Catalysis,2019,vol. 361,p. 2301 - 2308
[3]Journal of Fluorine Chemistry,2001,vol. 111,p. 1 - 10
[4]Angewandte Chemie - International Edition,2017,vol. 56,p. 9381 - 9385
Angew. Chem.,2017,vol. 129,p. 9509 - 9513,5

17
[ 75-36-5 ]
[ 371-40-4 ]
[ 351-83-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With triethylamine In dichloromethane at 0 - 20℃; for 0.5h;
93%	With hydroxyapatite supported copper(I) oxide In acetonitrile at 50℃; for 0.1h;	General procedure for N-acetylation of amines usingHAP-Cu2O General procedure: To a mixture of amine (1 mmol), acetyl chloride (1 mmol)in acetonitrile (5 mL) were added hydroxyapatite -Cu2O(0.1 g) under air atmosphere. The reaction mixture wasrefluxed at 50 °C for an appropriate time. The progress ofthe reaction was monitored through TLC. Upon completionof the reaction, the reaction mixture was cooled toroom temperature and filtered. The residue was washedwith water followed by EtOAc (3 × 10 mL). The productwas obtained after the removal of solvent under reducedpressure followed by crystallization from pet ether orEtOAc:pet ether or passing through column of silica andelution with EtOAc:pet ether.
92%	With triethylamine In diethyl ether at 0 - 20℃;

89%	With pyridine In toluene at 5℃;
	With N-ethyl-N,N-diisopropylamine In dichloromethane
	With pyridine In toluene cooling;
	With triethylamine In chloroform	P.17.1 Synthesis of 4-fluoro-N-(2-pyridyl)aniline 1) Triethylamine (31 ml) and acetyl chloride (15 ml) were added dropwise to a chloroform (100 ml) solution of 4-fluoroaniline (22.3 g) in this order under ice-cooling. The reaction mixture was stirred at room temperature for 2 hours and concentrated under reduced pressure. The thus-obtained solid was washed with water, collected by filtration, and recrystallized from ethanol-water to obtain colorless crystals of 4-fluoroacetanilide (25.5 g; yield, 83%).
	With pyridine In dichloromethane at 0℃; for 0.25h;	59 Example 59: 2,2,2-Trifluoro-l-[l-(4-fluorophenyl)-2-methyl-lH-benzimidazol-5-yl]-l-(l- methyl-lH-indol-3-yl)ethanol; To a chilled (ice-bath) solution of 4-fluorophenylamine (2.9 mL, 30 mmol) and anhydrous pyridine (3.7 mL, 45 mmol) in methylene chloride (50 mL) was slowly added a solution of acetyl chloride (2.4 mL, 33 mmol) in methylene chloride (10 mL). After 15 minutes, the mixture was concentrated in vacuo and the residue was diluted with cold water. The resulting precipitate was filtered, washed with water and dried to afford 4.2 g of N-(4- fluorophenyl)acetamide as an off white solid. MS m/z 154 (MH+).
	With triethylamine In dichloromethane at 0 - 20℃;
	With triethylamine In dichloromethane at 0℃; Inert atmosphere;
	With triethylamine In dichloromethane at 0 - 20℃;
	With triethylamine In dichloromethane at 20℃; Inert atmosphere; Cooling with ice;
	Stage #1: 4-fluoroaniline With triethylamine In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: acetyl chloride In dichloromethane at 0℃; for 0.25h; Inert atmosphere;
	With triethylamine In dichloromethane at 0 - 20℃; for 10h; Inert atmosphere;
	With dmap; triethylamine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;
	With triethylamine In dichloromethane at 0 - 20℃; Schlenk technique;

Reference： [1]Tilden, James A. R.; Lubben, Anneke T.; Reeksting, Shaun B.; Kociok-Köhn, Gabriele; Frost, Christopher G. [Chemistry - A European Journal, 2022, vol. 28, # 11]
[2]Gupta, Manjulla; Gupta, Monika [Journal of the Iranian Chemical Society, 2016, vol. 13, # 2, p. 231 - 241]
[3]Gonzalez-Gomez, Alvaro; Anorbe, Loreto; Poblador, Amalia; Dominguez, Gema; Perez-Castells, Javier [European Journal of Organic Chemistry, 2008, # 8, p. 1370 - 1377]
[4]Chakraborty, Kajal; Devakumar [Journal of Agricultural and Food Chemistry, 2005, vol. 53, # 20, p. 7899 - 7907]
[5]Walker, Michael A.; Johnson, Timothy; Ma, Zhuping; Zhang, Yunhui; Banville, Jacques; Remillard, Roger; Plamondon, Serge; Pendri, Annapurna; Wong, Henry; Smith, Daniel; Torri, Albert; Samanta, Himadri; Lin, Zeyu; Deminie, Carol; Terry, Brian; Krystal, Mark; Meanwell, Nicholas [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 22, p. 5818 - 5821]
[6]Chakraborty, Kajal; Devakumar [Journal of Agricultural and Food Chemistry, 2006, vol. 54, # 18, p. 6800 - 6808]
[7]Bergeot, Olga; Corsi, Camilla; El Qacemi, Myriem; Zard, Samir Z. [Organic and Biomolecular Chemistry, 2006, vol. 4, # 2, p. 278 - 290]
[8]Current Patent Assignee: JAPAN TOBACCO INC - US6235730, 2001, B1
[9]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2008/70507, 2008, A2 Location in patent: Page/Page column 161
[10]Kim, Byung Seok; Jang, Chungsik; Lee, Dong Jin; Youn, So Won [Chemistry - An Asian Journal, 2010, vol. 5, # 11, p. 2336 - 2340]
[11]Location in patent: experimental part Guerrini, Giacomo; Taddei, Maurizio; Ponticelli, Fabio [Journal of Organic Chemistry, 2011, vol. 76, # 18, p. 7597 - 7601]
[12]Zhang, Hao; Chen, Pinhong; Liu, Guosheng [Synlett, 2012, vol. 23, # 19, p. 2749 - 2752]
[13]Panini, Piyush; Chopra, Deepak [CrystEngComm, 2013, vol. 15, # 18, p. 3711 - 3733]
[14]Jiang, Jian; Zhang, Wen-Man; Dai, Jian-Jun; Xu, Jun; Xu, Hua-Jian [Journal of Organic Chemistry, 2017, vol. 82, # 7, p. 3622 - 3630]
[15]Shi, Yang; Liu, Jiahui; Yang, Yudong; You, Jingsong [Chemical Communications, 2019, vol. 55, # 38, p. 5475 - 5478]
[16]Liu, Feng; Wu, Na; Cheng, Xu [Organic Letters, 2021, vol. 23, # 8, p. 3015 - 3020]
[17]Chen, Xiaoyu; Guo, Zhuangzhuang; Li, Jingya; Wu, Yangjie; Wu, Yusheng; Xue, Yingying; Zou, Dapeng [Organic and Biomolecular Chemistry, 2022, vol. 20, # 5, p. 989 - 994]

18
[ 158364-41-1 ]
[ 351-83-7 ]

Yield	Reaction Conditions	Operation in experiment
97%	With 1,3,5-trichloro-2,4,6-triazine; zinc(II) chloride In acetonitrile for 2h; Heating;
97%	With N-fluorobis(benzenesulfon)imide; samarium(III) trifluoromethanesulfonate In acetonitrile at 110℃; for 0.333333h; Sealed tube; Microwave irradiation;	3. General procedures for the synthesis of amides 2a-2k General procedure: To a solution of the oxime substrates 1a-1k (0.2 mmol) in CH3CN (0.2 mL) were added a mixture of Sm(OTf)3 (1.2 mg, 0.002 mmol) and NFSI (9.5 mg, 0.03 mmol). Then the solution was heated to 100 °C under the microwave irradiation for 10 min. The solvent was removed in vacuo to afford a residue, which was purified by a flash column chromatography on silica gel to afford the products 2a-2k.
97%	With 2,2-dichloro-1,3-dicyclohexylimidazolidine-4,5-dione In acetonitrile at 80℃; for 0.166667h; Inert atmosphere; Schlenk technique;

95%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In tetrahydrofuran; ethyl acetate at 70℃; for 3h; Inert atmosphere;	20 T3P catalyzed synthesis of amides/lactams from ketoximes: To a solution of ketoxime (0.01 mol) in THF (10 mL) was added T3P (15 mol %, 50% soln in EtOAc) and the resulting reaction mixture was stirred at reflux for 1-4 h under nitrogen atmosphere. When the reaction was completed as confirmed by TLC, the solvent was removed under vacuum and the residue was diluted with water (20 mL). The product was extracted with ethyl acetate (2 × 20 mL) and the combined organic phase was washed with saturated NaHCO3 solution (1 × 10 mL) and brine. The organic phase was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to afford the desired amides in good purity.
41%	With 1,1,1,3',3',3'-hexafluoro-propanol; tetrabutylammonium tetrafluoroborate; water In 1,2-dichloro-ethane at 20℃; for 1.46667h; Electrochemical reaction;

Reference： [1]Furuya, Yoshiro; Ishihara, Kazuaki; Yamamoto, Hisashi [Journal of the American Chemical Society, 2005, vol. 127, # 32, p. 11240 - 11241]
[2]Xie, Fukai; Du, Chuan; Pang, Yadong; Lian, Xu; Xue, Chentao; Chen, Yanyu; Wang, Xuefei; Cheng, Maosheng; Guo, Chun; Lin, Bin; Liu, Yongxiang [Tetrahedron Letters, 2016, vol. 57, # 51, p. 5820 - 5824]
[3]Gao, Yu; Liu, Jingjing; Li, Zhenjiang; Guo, Tianfo; Xu, Songquan; Zhu, Hui; Wei, Fulan; Chen, Siming; Gebru, Hailemariam; Guo, Kai [Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 2040 - 2049]
[4]Location in patent: scheme or table Augustine, John Kallikat; Kumar, Rajesha; Bombrun, Agnes; Mandal, Ashis Baran [Tetrahedron Letters, 2011, vol. 52, # 10, p. 1074 - 1077]
[5]Tang, Li; Wang, Zhi-Lv; He, Yan-Hong; Guan, Zhi [ChemSusChem, 2020, vol. 13, # 18, p. 4929 - 4936]

19
[ 351-83-7 ]
[ 330-83-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: CuCl; K₂CO₃ / xylene 2: aq. NaOH / ethanol
	Multi-step reaction with 2 steps 1: K₂CO₃, CuI 2: KOH / ethanol; H₂O / 1.5 h / Heating

Reference： [1]Takamura, Fujiko; Tanaka, Akira; Takasugi, Hisashi; Taniguchi, Kiyoshi; Nishio, Mie; Seki, Jiro; Hattori, Kouji [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 17, p. 4475 - 4478]
[2]Cairi, M.; Gerig, J. T. [Journal of the American Chemical Society, 1984, vol. 106, # 12, p. 3640 - 3643]

20
[ 351-83-7 ]
[ 583-42-6 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 4906 - 4916

21
[ 351-83-7 ]
[ 345-17-5 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1916,vol. 35,p. 142
Chemisches Zentralblatt,1913,vol. 84,p. 760
[2]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1976,vol. 30,p. 141 - 149

22
[ 351-83-7 ]
[ 343-54-4 ]

Reference： [1]Journal of the Chemical Society,1948,p. 288,290

23
[ 351-83-7 ]
[ 343-26-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sulfuric acid 2: aqueous hydrochloric acid 3: concentrated sulfuric acid; arsenic (V)-oxide

Reference： [1]Wilkinson; Finar [Journal of the Chemical Society, 1948, p. 288,290]

24
[ 351-83-7 ]
[ 446-09-3 ]

Reference： [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1976,vol. 30,p. 141 - 149

25
[ 673-32-5 ]
[ 351-83-7 ]
[ 1092102-07-2 ]

Yield	Reaction Conditions	Operation in experiment
74%	With [Cp*Rh(MeCN)3][SbF₆]2; oxygen; copper(II) acetate monohydrate In tert-Amyl alcohol at 60℃; for 16h;
47%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate In tert-Amyl alcohol at 120℃; for 3h;

Reference： [1]Stuart, David R.; Alsabeh, Pamela; Kuhn, Michelle; Fagnou, Keith [Journal of the American Chemical Society, 2010, vol. 132, # 51, p. 18326 - 18339]
[2]Stuart, David R.; Bertrand-Laperle, Megan; Burgess, Kevin M. N.; Fagnou, Keith [Journal of the American Chemical Society, 2008, vol. 130, # 49, p. 16474 - 16475]

26
[ 101251-09-6 ]
[ 351-83-7 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 2860 - 2863

27
[ 1222195-93-8 ]
[ 351-83-7 ]
[ 1222195-94-9 ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: 4'-fluoroacetanilide With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #2: C₇⁽¹³⁾C₃H₁₀O₃S In tetrahydrofuran; hexane at -78 - 20℃; for 6h; Inert atmosphere;

Reference： [1]Neukom, Joshua D.; Perch, Nicholas S.; Wolfe, John P. [Journal of the American Chemical Society, 2010, vol. 132, p. 6276 - 6277]

28
[ 351-83-7 ]
[ 292638-85-8 ]
[ 1259100-53-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver trifluoromethanesulfonate; silver carbonate In 1,2-dichloro-ethane at 90℃; for 12h; chemoselective reaction;
77%	With tert.-butylhydroperoxide; palladium(II) trifluoroacetate; silver trifluoromethanesulfonate In toluene at 120℃; for 24h;	2.1. Typical procedure for the synthesis of anilides with olefins: General procedure: The mixture of 4-methyl-N-phenylbenzamide (1a) (0.5 mmol), ethyl Acrylate (2a) (0.7 mmol), Pd (TFA)2 (5 mol%), AgOTf (25 mol%) and TBHP (1.5 equiv.) in toluene (3 mL) was stirred at 120 °C under air for 24 h. Upon completion, the reaction mixture was removed the solvents to give the residue. The residue was then purified by column chromatography on silica gel (ethyl acetate / petroleum ether = 1:10) to provide the corresponding product as white solid 3a.
76%	With dipotassium peroxodisulfate; palladium diacetate; trifluoroacetic acid In dichloromethane at 25℃; for 48h;

Reference： [1]Wang, Dawei; Yu, Xiaoli; Xu, Xiang; Ge, Bingyang; Wang, Xiaoli; Zhang, Yaxuan [Chemistry - A European Journal, 2016, vol. 22, # 25, p. 8663 - 8668]
[2]Yu, Xiaoli; Yao, Wei; Wan, Huida; Xu, Zhaojun; Wang, Dawei [Journal of Organometallic Chemistry, 2016, vol. 822, p. 100 - 103]
[3]Kim, Byung Seok; Jang, Chungsik; Lee, Dong Jin; Youn, So Won [Chemistry - An Asian Journal, 2010, vol. 5, # 11, p. 2336 - 2340]

29
4-(triethoxysilyl)acetanilide [ No CAS ]
[ 351-83-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	With Selectfluor; barium(II) oxide; silver(l) oxide In acetone at 23 - 90℃; for 2h; regioselective reaction;	4.3.2. General procedure B (for non-volatile compounds) General procedure: To aryl silane (0.100 mmol, 1.00 equiv) in acetone (2.0 mL) at 23 °C were added silver oxide (46.4 mg, 0.200 mmol, 2.00 equiv), barium oxide (17.2 mg, 0.110 mmol, 1.10 equiv) or 2,6-lutidine (12.8 μL, 0.110 mmol, 1.10 equiv) and 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (1) (70.8 mg, 0.200 mmol, 2.00 equiv). The reaction mixture was stirred for 2 h at 90 °C in a sealed vial. The reaction mixture was cooled to 23 °C and concentrated under reduced pressure. To the residue was added CH2Cl2 and the mixture was filtered through a pad of Celite eluting with CH2Cl2. The filtrate was concentrated under reduced pressure and the residue was purified by chromatography on silica gel or preparative TLC.

Reference： [1]Tang, Pingping; Ritter, Tobias [Tetrahedron, 2011, vol. 67, # 24, p. 4449 - 4454]

30
[ 351-83-7 ]
[ 2343-25-1 ]

Yield	Reaction Conditions	Operation in experiment
49 mg	In acetonitrile at 20℃; for 20h; Inert atmosphere; UV-irradiation;
	With nitriding Carbon In 1,4-dioxane at 40℃; for 44h; Inert atmosphere; Irradiation;	1.1; 2.1 Preparation of 2-amino-5-fluoroacetophenone: Under the protection of argon atmosphere, add 15.3g (100mmol) of 4-fluoroacetanilide (Compound 4) and 200mL of dioxane solvent to a 500mL single-necked flask with magnetic stir bar, then add 306mg of visible light catalyst for nitriding Carbon (g-C3N4) (w / w = 2.35%), heated to 40 under stirring, while a 36-watt LED lamp was used to photocatalyze the Fries rearrangement reaction to the light of the reaction system, and the reaction system was kept at The reaction was carried out under light for 44h. After the raw material reaction was completed, the temperature was lowered to room temperature. The reaction solution was filtered through celite to remove the visible light catalyst and filtered with suction. The filter residue was washed with 50mL of dioxane. The filtrate was collected. The filtrate was concentrated under reduced pressure to remove solvent 2. Oxygen hexacyclo to give 15.3g of brownish yellow solid. This crude product is 2-amino-5-fluoroacetophenone (compound 5). This product is used as raw material for the next reaction without purification. The yield is calculated as 100% ;

Reference： [1]Location in patent: experimental part Guerrini, Giacomo; Taddei, Maurizio; Ponticelli, Fabio [Journal of Organic Chemistry, 2011, vol. 76, # 18, p. 7597 - 7601]
[2]Current Patent Assignee: CHANGZHOU INSTITUTE OF TECHNOLOGY - CN110922315, 2020, A Location in patent: Paragraph 0033-0036; 0043-0045

31
[ 403-42-9 ]
[ 329-79-3 ]
[ 351-83-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 78% 2: 6%	With acetylhydroxamic acid; sulfuric acid In acetonitrile at 80℃; for 0.166667h; Microwave irradiation;	Typical procedure for the preparation of amide under microwave heating: General procedure: Acetophenone 1a (1.0 g, 8.3 mmol), acetohydroxamic acid (0.92 g, 12.5 mmol), acetonitrile (3 ml), and conc. H2SO4 (0.2 ml) were taken into a 10 ml pressure tube and subjected to microwave heating (CEM discover, 360 W, 80 °C, 25 psi) for 10 min. The crude product obtained was purified as mentioned above to afford acetanilide 2a (0.94 g, 86%) and it gave spectral data same as above.

Reference： [1]Location in patent: experimental part Madabhushi, Sridhar; Chinthala, Narsaiah; Vangipuram, Venkata Sairam; Godala, Kondal Reddy; Jillella, Raveendra; Mallu, Kishore Kumar Reddy; Beeram, China Ramanaiah [Tetrahedron Letters, 2011, vol. 52, # 46, p. 6103 - 6107]

32
[ 141-32-2 ]
[ 351-83-7 ]
[ 1351459-36-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With palladium 10% on activated carbon; toluene-4-sulfonic acid; p-benzoquinone In water at 85℃; Flow reactor;
80%	With palladium 10% on activated carbon; oxygen; toluene-4-sulfonic acid; p-benzoquinone at 85℃; for 3.33333h; Flow reactor; Green chemistry; regioselective reaction;
53%	With potassium hexafluorophosphate; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; copper(II) acetate monohydrate In water at 120℃; for 20h; Inert atmosphere;

48%

With oxygen In toluene at 80℃; for 16h;

Reference： [1]Ferlin, Francesco; Santoro, Stefano; Ackermann, Lutz; Vaccaro, Luigi [Green Chemistry, 2017, vol. 19, # 11, p. 2510 - 2514]
[2]Ferlin, Francesco; Anastasiou, Ioannis; Carpisassi, Luigi; Vaccaro, Luigi [Green Chemistry, 2021, vol. 23, # 17, p. 6576 - 6582]
[3]Ackermann, Lutz; Wang, Lianhui; Wolfram, Ratnakancana; Lygin, Alexander V. [Organic Letters, 2012, vol. 14, # 3, p. 728 - 731]
[4]Chng, Leng Leng; Zhang, Jie; Yang, Jinhua; Amoura, Makhlouf; Ying, Jackie Y. [Advanced Synthesis and Catalysis, 2011, vol. 353, # 16, p. 2988 - 2998]

33
[ 351-83-7 ]
[ 120801-75-4 ]
[ 1354550-02-9 ]

Yield	Reaction Conditions	Operation in experiment
72%	With Br^(1-)*C₂₁H₂₆N₃S⁽¹⁺⁾; sodium carbonate In toluene at 80℃; for 0.4h;	4.3.1. Typical procedure for synthesizing difluoromethyl imidates General procedure: To a toluene solution (1.5 mL) of 4·HBr (3.4 mg, 0.0098 mmol), sodium carbonate (4.2 mg, 0.040 mmol), and N-phenylcyclohexanecarboxamide 7d (39 mg, 0.19 mmol) was added TFDA (75 μL, 0.38 mmol) at room temperature. The reaction mixture was stirred and heated at 80 °C for 20 min. After cooling the resulting mixture to room temperature, aquaus NaOH was added to quench the reaction. Extraction with dichloromethane and purification by column chromatography (SiO2, hexane:AcOEt = 50:1, 0 °C) gave 8d (39 mg, 81% yield).

Reference： [1]Location in patent: experimental part Fuchibe, Kohei; Koseki, Yuta; Aono, Tatsuya; Sasagawa, Hisashi; Ichikawa, Junji [Journal of Fluorine Chemistry, 2012, vol. 133, p. 52 - 60]

34
[ 3240-34-4 ]
[ 103-84-4 ]
[ 351-83-7 ]
[ 2623-33-8 ]
[ 32047-92-0 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 728 - 732

35
[ 351-83-7 ]
[ 95-50-1 ]
[ 877179-03-8 ]

Yield	Reaction Conditions	Operation in experiment
45%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; cesium pivalate; Trimethylacetic acid at 130℃; for 19h;	1 Example 1 Coupling of N-(4-fluorophenyl)acetamide with 1,2-dichlorobenzene in the presence of [RhCpCl2]2 Example 1 Coupling of N-(4-fluorophenyl)acetamide with 1,2-dichlorobenzene in the presence of [RhCpCl2]2 153.2 mg (1.00 mmol) of N-(4-fluorophenyl)acetamide, 15.5 mg (0.02 mmol) of [RhCp*Cl2]2, 34.4 mg (0.10 mmol) of AgSbF6, 399.6 mg (2.20 mmol) of Cu(OAc)2, 112.3 mg (1.10 mmol) of PivOH and 46.8 mg (0.2 mmol) of CsOPiv were initially charged with exclusion of oxygen in a baked-out Radley reaction tube, and 5.0 ml (44.4 mmol) of 1,2-dichlorobenzene were added. The reaction mixture was stirred at 130° C. for 19 hours. After the reaction had ended (HPLC monitoring), the reaction mixture was cooled to RT, filtered through a short silica gel column and eluted with EtOAc. The solvent was removed by distillation and the crude product was purified by means of preparative HPLC. This gave 134.0 mg of N-(3',4'-dichloro-5-fluorobiphenyl-2-yl)acetamide with an LC purity of 99.9% (45% yield).
45%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; cesium pivalate; Trimethylacetic acid at 130℃; for 19h;	1 Coupling of N-(4-fluorophenyl)acetamide with 1,2-dichlorobenzene in the presence of [RhCpCl2]2 Example 1 Coupling of N-(4-fluorophenyl)acetamide with 1,2-dichlorobenzene in the presence of [RhCpCl2]2 153.2 mg (1.00 mmol) of N-(4-fluorophenyl)acetamide, 15.5 mg (0.02 mmol) of [RhCp*Cl2]2, 34.4 mg (0.10 mmol) of AgSbF6, 399.6 mg (2.20 mmol) of Cu(OAc)2, 112.3 mg (1.10 mmol) of PivOH and 46.8 mg (0.2 mmol) of CsOPiv were initially charged with exclusion of oxygen in a baked-out Radley reaction tube, and 5.0 ml (44.4 mmol) of 1,2-dichlorobenzene were added. The reaction mixture was stirred at 130° C. for 19 hours. After the reaction had ended (HPLC monitoring), the reaction mixture was cooled to RT, filtered through a short silica gel column and eluted with EtOAc. The solvent was removed by distillation and the crude product was purified by means of preparative HPLC. This gave 134.0 mg of N-(3',4'-dichloro-5-fluorobiphenyl-2-yl)acetamide with an LC purity of 99.9% (45% yield).
25%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; hexabromobenzene; 2-chloro-1,4-dimethyl-benzene; copper diacetate; cesium pivalate; Trimethylacetic acid at 140℃; for 21h; Inert atmosphere;

Reference： [1]Current Patent Assignee: BAYER AG - US2015/203440, 2015, A1 Location in patent: Paragraph 0183
[2]Current Patent Assignee: BAYER AG - US9199915, 2015, B2 Location in patent: Page/Page column 17
[3]Wencel-Delord, Joanna; Nimphius, Corinna; Wang, Honggen; Glorius, Frank [Angewandte Chemie - International Edition, 2012, vol. 51, # 52, p. 13001 - 13005][Angew. Chem., 2012, vol. 124, # 54, p. 13175 - 13180,6]

36
[ 766-98-3 ]
[ 351-83-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	With trimethylsilylazide; silver carbonate; trifluoroacetic acid In water; 1,2-dichloro-ethane at 60℃; for 12h; Schlenk technique; Inert atmosphere;
81%	With (triphenylphosphine)gold(I) chloride; trimethylsilylazide; water; silver carbonate; trifluoroacetic acid In 1,2-dichloro-ethane at 60℃; Schlenk technique; Inert atmosphere;
74%	With formic acid; nitromethane; trifluoromethylsulfonic anhydride In acetic acid at 100℃; for 12h;

68%

With sodium azide; C₁₆H₁₇AuBrN₃O; water; trifluoroacetic acid In 1,2-dichloro-ethane at 25℃; for 2h; Schlenk technique; Inert atmosphere; regioselective reaction;

6.3. General procedure for catalysis General procedure: Alkynes (0.5 mmol), NaN3 (1 mmol), H2O (1 mmol), catalyst 1(2 mol%) and TFA/DCE (2 mL, 1:1 v/v) were taken in a Schlenk tube inside a fume hood. The reaction mixture was allowed to stir for 2 h at room temperature. Then 25 mL water was added to it and theorganics were extracted with ethyl acetate (3 x 10 mL). The solventwas evaporated under reduced pressure. The residue was purifiedby column chromatography on silica gel (petroleum ether/ethylacetate) to give the desired amide product. Yields were calculatedbased on isolated products. GC yields were reported in presence ofinternal standard dodecane.

Reference： [1]Nie, Quan; Yi, Feiyan; Huang, Bin; Cai, Mingzhong [Advanced Synthesis and Catalysis, 2017, vol. 359, # 22, p. 3968 - 3976]
[2]Qin, Chong; Feng, Peng; Ou, Yang; Shen, Tao; Wang, Teng; Jiao, Ning [Angewandte Chemie - International Edition, 2013, vol. 52, # 30, p. 7850 - 7854][Angew. Chem., 2013, vol. 125, # 30, p. 8004 - 8008]
[3]Jiao, Ning; Liu, Jianzhong; Qiu, Xu; Song, Song; Wei, Jialiang; Wen, Xiaojin; Zhang, Cheng; Zhang, Ziyao [Science, 2020, vol. 367, # 6475, p. 281 - 285]
[4]Singh, Kuldeep; Pal, Nilay Kumar; Guha, Chirajyoti; Bera, Jitendra K. [Journal of Organometallic Chemistry, 2019, vol. 886, p. 1 - 8]

37
[ 351-83-7 ]
[ 4280-34-6 ]
C₈H₈FN [ No CAS ]
[ 405-67-4 ]
[ 347-39-7 ]
[ 371-40-4 ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 11039 - 11050

38
[ 60-35-5 ]
[ 352-34-1 ]
[ 351-83-7 ]

Yield	Reaction Conditions	Operation in experiment
73%	With copper(I) thiophene-2-carboxylate; sodium tertiary butoxide In dimethyl sulfoxide at 100℃; for 6h; Inert atmosphere;
65%	With Cupric sulfate; sodium (R)-5-((S)-1,2-dihydroxyethyl)-4-hydroxy-2-oxo-2,5-dihydrofuran-3-olate; sodium tertiary butoxide In dimethyl sulfoxide at 100℃; for 7h;	1 General procedure for N-arylation of primary amides General procedure: CuSO4*5H2O (0.15 mmol), NaAsc (0.3 mmol), aryl iodides (1mmol), primary amides (1.2mmol), t-BuONa (2.0 mmol), and DMSO (3mL) were added to a flask. The reaction mixture was stirred under air, and then cooled to room temperature and extracted with ethyl acetate (3×10 mL). The organic layer was then dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure. The secondary amides were finally obtained by column chromatography on silica gel eluted with ethyl acetate/petroleum ether.
57%	With copper carbonate hydroxide; Cs₂CO₃; Ethane-1,2-diamine In 2-methyltetrahydrofuran at 110℃; for 24h; Sealed tube;	4.2 General procedure for the preparationof N-arylamides 3 General procedure: The corresponding aryl halide (1, 3.00 mmol) and amide(2, 3.60 mmol) were dissolved in 2-MeTHF (6 mL) in a40-mL vial, then 1,2-ethylenediamine (EDA, 3.00 mmol),Cs2CO3(7.50 mmol) and malachite (50.0 mg, 13.0 mol%)were added to this solution. The vial was then sealed with astopper and the reaction was stirred for 24 h at 110 °C. Themixture was then filtered, then washed with EtOAc (60 mL).After evaporation of the filtrate, the residue was purifiedby flash column chromatography. An analytical sample wasrecrystallized from the solvent given below after the meltingpoint. Compounds 3a-g, 3i-l and 3o-an are known in theliterature, while compounds 3h,m,n are new.

Reference： [1]Quan, Zheng-Jun; Xia, Hai-Dong; Zhang, Zhang; Da, Yu-Xia; Wang, Xi-Cun [Applied Organometallic Chemistry, 2014, vol. 28, # 2, p. 81 - 85]
[2]Quan, Zheng-Jun; Xia, Hai-Dong; Zhang, Zhang; Da, Yu-Xia; Wang, Xi-Cun [Tetrahedron, 2013, vol. 69, # 39, p. 8368 - 8374]
[3]Bezúr, László; Dancsó, András; Györke, Gábor; Hunyadi, Dávid; Milen, Mátyás; Szalóki, Imre; Volk, Balázs [Catalysis Letters, 2022]

39
[ 60-35-5 ]
[ 460-00-4 ]
[ 351-83-7 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium phosphate; copper(l) iodide; C₈H₁₆N₂O*C₂H₂O₄; potassium iodide In N,N-dimethyl-formamide at 130℃; Inert atmosphere;	Amidation using 18(oxalate) General procedure: To an ovendried round bottom flask, equipped with stir bar, was added 0.3 equiv. CuI, 1equiv KI, 0.6 equiv iPr Pro Amide•oxalate , and 4 equiv. K3PO4. The flask was topped witha rubber septum, fitted with a temperature probe, and sealed with electricaltape. N2 was blown across the solids for ≥ 30 minutes. After thistime, 7.5 mL dry DMF was added to the flask along with 1 g of Aryl bromide. Thereaction vessel was placed into a preheated oil bath and, upon reaching aninternal temperature of 130 °C, was allowed to stir for 5h. After 5h, thereaction was removed from the oil bath and allowed to cool to ambient temperature.Once cooled, 15 vol ethyl acetate were added and the solids filtered off,rinsing the solids with 3x5vol ethyl acetate. Next, 15 vol saturated aqueous NH4Cl,4.4 g LiCl, and 10 mL saturated NaCl solution. The entire biphasic mixture wasallowed to stir for 1h. After 1h, the organics were separated from the aqueous.The aqueous was back extracted with 15 vol ethyl acetate (3-6x). The combinedorganics were washed 1x10 vol satd. LiCl solution. The organics were then driedover Na2SO4. Finally, the organics were decanted,concentrated en vacuo, and purifiedby flash chromatography.

Reference： [1]Mitra, Aurpon W.; Hansen, Marvin M.; Laurila, Michael E.; Kolis, Stanley P.; Martinelli, Joseph R. [Tetrahedron Letters, 2013, vol. 54, # 48, p. 6580 - 6583]

40
[ 123-54-6 ]
[ 371-40-4 ]
[ 351-83-7 ]

Yield	Reaction Conditions	Operation in experiment
94%	With dihydrogen peroxide In water at 25℃; for 8h; Green chemistry;
58%	With 2,2'-azobis(isobutyronitrile); oxygen In acetonitrile at 80℃; for 24h; Sealed tube;	9 General procedure for AIBN-promoted oxidative formation of amides from amines and 1, 3-diketones (3a) General procedure: A sealed tube was equipped with a magnetic stir bar was charged with 1,3-di-ketone 1a (0.075 g, 0.75 mmol), aniline 2a (0.0232 g, 0.25 mmol), AIBN (0.0164 g, 0.0001 mmol), and acetonitrile (1.0 mL). The above reaction mixture was stirred at 80°C under O2 atmosphere for 24 h. After completion of the reaction, the reaction was then cooled to room temperature, mixture was diluted with ethyl acetate. After removal of the solvent under reduced pressure the left out residue was purified by column chromatography using silica gel with hexane and ethyl acetate as eluent to get 3a in 82% yield (0.0278 g). The spectral data was well matched with reported values. The above procedure is followed for the synthesis of all products reported in this manuscript.

Reference： [1]Sun, Xi; Wang, Min; Li, Pinhua; Zhang, Xiuli; Wang, Lei [Green Chemistry, 2013, vol. 15, # 12, p. 3289 - 3294]
[2]Rao, Sadu Nageswara; Mohan, Darapaneni Chandra; Adimurthy, Subbarayappa [Tetrahedron, 2016, vol. 72, # 32, p. 4889 - 4894]

41
[ 351-83-7 ]
[ 292638-85-8 ]
[ 22614-75-1 ]

Yield	Reaction Conditions	Operation in experiment
54%	Stage #1: 4'-fluoroacetanilide; acrylic acid methyl ester With silver hexafluoroantimonate; [RhCl₂(p-cymene)]2; copper(II) acetate monohydrate In 1,2-dichloro-ethane; isopropyl alcohol at 110℃; for 12h; Inert atmosphere; Glovebox; Stage #2: With hydrogenchloride In water; 1,2-dichloro-ethane; isopropyl alcohol at 130℃; for 10h; Sealed tube;

Reference： [1]Manikandan, Rajendran; Jeganmohan, Masilamani [Organic Letters, 2014, vol. 16, # 13, p. 3568 - 3571]

42
[ 351-83-7 ]
[ 2926-29-6 ]
[ 393-23-7 ]

Yield	Reaction Conditions	Operation in experiment
63%	With palladium diacetate In dimethyl sulfoxide at 25℃; for 20h; Irradiation;
55%	With tert.-butylhydroperoxide In dichloromethane; water at 0 - 15℃; for 360h;
55%	With tert.-butylhydroperoxide In dichloromethane; water at 0 - 15℃; for 120h;	I Synthesis of 2-trifluoromethyl-4-fluoroacetanilide Fluoroacetanilide IIa (0.1538, 1.0 mol) and sodium trifluoromethanesulfinate (65%, 0.7208,Was added to a mixed solvent of 5 mL of dichloromethane (DCM) and 2 mL of water. A solution of tert-butyl hydroperoxide (70% aqueous solution, 0.68 mL, 5.0 mmol) was added dropwise very slowly at 0 ° C. The reaction was slowly allowed to rise to 5 ° C to 15 ° C, and the reaction was continued at that temperature for about 5 days. The reaction progress was followed by TLC. After completion of the reaction, the reaction mixture was extracted with 30 mL of ethyl acetate, washed with saturated sodium carbonate and dried over anhydrous sodium sulfate. After standing still for a while, the solvent was distilled off under reduced pressure to obtain a residue. The solvent used for purification and separation was obtained by using petroleum ether: ethyl acetate = 2: 1 (v / v) to give compound la (white solid),Yield 55%.

Reference： [1]Zou, Long; Li, Pinhua; Wang, Bin; Wang, Lei [Chemical Communications, 2019, vol. 55, # 26, p. 3737 - 3740]
[2]Wu, Mingxi; Ji, Xinfei; Dai, Wenpeng; Cao, Song [Journal of Organic Chemistry, 2014, vol. 79, # 19, p. 8984 - 8989]
[3]Current Patent Assignee: EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN104072324, 2016, B Location in patent: Paragraph 0023-0026

43
[ 1216902-36-1 ]
[ 142-71-2 ]
[ 351-83-7 ]

Yield	Reaction Conditions	Operation in experiment
64%	With carbon monoxide; palladium diacetate In acetonitrile at 60℃;	4.5 General procedure for the synthesis of acetanilides from guanidines General procedure: To a screw-cap reaction tube was added symmetrical N,N′-disubstituted guanidines 1a (0.2 mmol), Pd(OAc)2 (5 mol%, 2.2 mg), Cu(OAc)2 (0.2 mmol, 36.3 mg). The reaction tube was evacuated and back-filled with CO (three times, balloon). MeCN (2mL) was added using a syringe and the mixture was heated to the desired temperature with use of an oil bath. When the reaction was completed (detected by TLC), the mixture was cooled to room temperature and vented to discharge the excess CO. The solvent was concentrated by evaporation in vacuo. The residue was purified by flash column chromatography on silica gel to afford the desired product amides 2a with petroleum ether/ethyl acetate as the eluent.

Reference： [1]Chang, Denghu; Zhu, Dan; Zou, Peng; Shi, Lei [Tetrahedron, 2015, vol. 71, # 11, p. 1684 - 1693]

44
[ 351-83-7 ]
[ 151169-75-4 ]
[ 877179-03-8 ]

Yield	Reaction Conditions	Operation in experiment
63%	With silver hexafluoroantimonate; (p-cymene)ruthenium(II) chloride; copper(II) bis(trifluoromethanesulfonate); silver(l) oxide In N,N-dimethyl-formamide at 110℃; for 20h; Inert atmosphere; Sealed tube;
63%	With silver hexafluoroantimonate; (p-cymene)ruthenium(II) chloride; copper(II) bis(trifluoromethanesulfonate); silver(l) oxide In N,N-dimethyl-formamide at 110℃; for 20h; Inert atmosphere; Sealed tube;	7 N-(3',4'-dichloro-5-fluoro-[1,1'-biphenyl-2-yl)acetamide In a baffled, closable reaction vessel, a solution comprising Ν-(4-fluorophenyl)acetamide (153 Mg, 1.0 mmol), [{RuC12 (p-isopropyltoluene)} 2] (30.6 mg, 5.0 mol %), AgSbF6 (68.7 mg, 0.2 mmol), Ag20 (232 mg, 1.0 mmol), Cu (OTf) 2 (72.3 mg, 0.2 mmol) and 3,4-dichlorophenylboronic acid (286 mg, 1.5 mmol) in anhydrous DMF (3.0 mL) was stirred at 110 ° C under a nitrogen atmosphere Stir for 20 hours. The reaction mixture was then treated with EtOAc (75 mL) at room temperature Diluted with water and filtered through celite and silica gel, and the filtrate was concentrated. Will be so obtained The crude product was purified by chromatography on silica gel (n-hexane / EtOAc: 7/3). To obtain 188 mg of N- (3 ', 4'-dichloro-5-fluoro- [1,1'-biphenyl] -2-yl) Acetamide (63% of theory)

Reference： [1]Hubrich, Jonathan; Himmler, Thomas; Rodefeld, Lars; Ackermann, Lutz [Advanced Synthesis and Catalysis, 2015, vol. 357, # 2-3, p. 474 - 480]
[2]Current Patent Assignee: BAYER AG - TW2016/4175, 2016, A Location in patent: Page/Page column 21

45
[ 351-83-7 ]
[ 925-90-6 ]
[ 2146-07-8 ]
[ 78-93-3 ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: 4'-fluoroacetanilide With 2-fluoropyridine; trifluoromethylsulfonic anhydride In dichloromethane at 0℃; for 0.5h; Stage #2: ethylmagnesium bromide With cerium(III) chloride In tetrahydrofuran; dichloromethane at -78℃; for 2h; Stage #3: With hydrogenchloride In ethyl acetate	General procedure for N-deacylation of secondary amides General procedure: Tf2O (185μL, 1.1mmol) was added dropwise to a cooled (0°C) solution of amide (1.0mmol) and 2-fluoropyridine (103μL, 1.2mmol) in dichloromethane (4mL). After stirring at 0°C for 30min, the mixture was cannulated to a freshly prepared organocerium reagent/complex (3.0mmol) in THF (15mL) at -78°C and stirred for 2h. Aqueous HCl solution (3mol/L, 5mL) was added to quench the reaction and the mixture was allowed to warm to r.t. and stirred for 2h. Ammonium hydroxide solution (25%, 5mL) was then added to the mixture. The organic layer was separated and the aqueous phase was extracted with diethyl ether (3× 10mL). The combined organic layers were washed with brine (3× 3mL) and concentrated under reduced pressure to about 1/3 volume. The residual organic phase was then extracted with aqueous HCl solution (3mol/L, 3× 5mL). The separated organic phase was washed with brine (5mL), dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel to afford ketone. The aqueous phases were combined, washed with diethyl ether (5mL), basified with an ammonium hydroxide solution (25%, 5mL) and back-extracted with diethyl ether (5× 20mL). The ether layers were combined, washed with brine (5mL), dried over anhydrous MgSO4, filtered, acidified with a solution of HCl in ethyl acetate (3mol/L, 5mL) and concentrated under reduced pressure to afford the desired amine hydrochloride salt.

Reference： [1]Wang, Ai-E.; Chang, Zong; Liu, Yong-Peng; Huang, Pei-Qiang [Chinese Chemical Letters, 2015, vol. 26, # 9, p. 1055 - 1058]

46
[ 32833-96-8 ]
[ 351-83-7 ]
[ 49579-56-8 ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 1286 - 1289

47
[ 371-40-4 ]
[ 10387-40-3 ]
[ 351-83-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	With tetrabutylammonium tetrafluoroborate In ethyl acetate at 20℃; for 24h; Electrochemical reaction;
85%	With copper(II) acetate monohydrate In acetonitrile at 80℃; for 18h; Sealed tube;	Typical procedure for acetylation of phenols and anilines General procedure: Under air atmosphere, anilines or phenols (0.5 mmol), potassium thioacetate (3.0 eq.),Cu(OAc)2H2O (0.2 eq.), MeCN (3 mL) were added to a screw-capped vial. Thereaction vial was placed in a temperature-controlled oil bath pot set at 80 °C. Thereaction progress was monitored by TLC. After the completion of the reaction, thevial was removed from the oil bath pot and was left to cool to the ambient temperature.The solution was filtered though a short column of silica gel and washed with EtOAc.The filtrate was concentrated under reduced pressure to leave a crude product, whichwas purified by flash column chromatography on silica gel with Petroleumether/EtOAc as an eluent to give the desired product.
84%	With tris(2,2'-bipyridyl)ruthenium dichloride In acetonitrile at 20℃; Irradiation;

66%

With tert.-butylnitrite In acetonitrile at 25℃; for 4h;

3 Example 3: Synthesis of 4-fluoroacetanilide Add 2 mL of acetonitrile, 33.3 mg of p-fluoroaniline, 68.4 mg of potassium thioacetate, and 6.2 mg of tert-butyl nitrite to a 25 mL reaction tube, and react with magnetic stirring at 25° C. for 4 hours. After the reaction is over, extract with ethyl acetate, combine the organic phases, evaporate most of the solvent under reduced pressure, and perform column chromatography on the remaining mixture with petroleum ether and ethyl acetate combined with a 10:1 composition as the eluent After separation and purification, the desired product is obtained as a light yellow solid, 30.3 mg, with a yield of 66%.

Reference： [1]Tang, Li; Matuska, Jack H.; Huang, Yu-Han; He, Yan-Hong; Guan, Zhi [ChemSusChem, 2019, vol. 12, # 12, p. 2570 - 2575]
[2]Zhang, Jieyu; Ke, Qiumin; Tian, Feitao; Jiang, Bei; Ji, Chang-An; Zhang, Lingling; Yu, Jian; Huang, Dayun; Yan, Guobing [Synlett, 2019, vol. 30, # 6, p. 726 - 730]
[3]Liu, Hongxin; Zhao, Liyun; Yuan, Yunfei; Xu, Zhifang; Chen, Kai; Qiu, Shengxiang; Tan, Haibo [ACS Catalysis, 2016, vol. 6, # 3, p. 1732 - 1736]
[4]Current Patent Assignee: UNIV LISHUI - CN109456221, 2021, B Location in patent: Paragraph 0024-0028

48
[ 351-83-7 ]
[ 501-65-5 ]
6-fluoro-2-methyl-3,4-diphenylquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With silver hexafluoroantimonate; boron trifluoride diethyl etherate; [CoCp*(CO)I₂]; iron(II) acetate In 1,2-dichloro-ethane at 135℃; for 12h; Inert atmosphere;
70%	Stage #1: 4'-fluoroacetanilide With 2,6-dichloropyridine; trifluoromethylsulfonic anhydride In 1,2-dichloro-ethane at -78 - 0℃; for 0.416667h; Inert atmosphere; Stage #2: diphenyl acetylene In dichloromethane; 1,2-dichloro-ethane at 90℃; for 14h; Inert atmosphere; regioselective reaction;

Reference： [1]Lu, Qingquan; Vásquez-Céspedes, Suhelen; Gensch, Tobias; Glorius, Frank [ACS Catalysis, 2016, vol. 6, # 4, p. 2352 - 2356]
[2]Li, Lian-Hua; Niu, Zhi-Jie; Liang, Yong-Min [Chemistry - A European Journal, 2017, vol. 23, # 61, p. 15300 - 15304]

49
[ 351-83-7 ]
[ 623-48-3 ]
[ 56341-41-4 ]

Yield	Reaction Conditions	Operation in experiment
78%	With silver(I) acetate; palladium diacetate; trifluoroacetic acid at 120℃; for 24h; Sealed tube; Inert atmosphere; Schlenk technique;	Oxindoles 3 from Anilides 1 and Ethyl 2-Iodoacetate (2a); General Procedure General procedure: A seal-tube (15 mL) initially fitted with a septum containing anilide 1 (0.5 mmol), Pd(OAc)2 (11.3 mg, 0.05 mmol, 10 mol%), and AgOAc (83.5 mg, 0.5 mmol) was evacuated and purged with N2 three times. TFA (4.0 mL), and ethyl 2-iodoacetate (2a; 160 mg, 0.75 mmol) were added to the system and the reaction mixture was stirred at 120 °C for 24 h. The mixture was cooled to r.t. and filtered through a short Celite pad and washed with CH2Cl2 several times. The filtrate was concentrated under vacuum and purified on a silica gel column using hexane/EtOAc as eluent to give the corresponding pure oxindole product 3.

Reference： [1]Gandeepan, Parthasarathy; Rajamalli, Pachaiyappan; Cheng, Chien-Hong [Synthesis, 2016, vol. 48, # 12, p. 1872 - 1879]

50
[ 610-97-9 ]
[ 351-83-7 ]
[ 157848-52-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With silver(I) acetate; palladium diacetate; trifluoroacetic acid at 120℃; for 24h; Sealed tube; Inert atmosphere; Schlenk technique;	Phenanthridones 6 from Anilides 1 and 2-Iodobenzoates 5; General Procedure General procedure: A seal-tube (15 mL) initially fitted with a septum containing anilide 1 (0.5 mmol), Pd(OAc)2 (11.3 mg, 0.050 mmol, 10 mol%), and AgOAc (83.5 mg, 0.50 mmol) was evacuated and purged with N2 three times. TFA (4.0 mL) and 2-iodobenzoate 5 (0.75 mmol) were added to the system and the reaction mixture was stirred at 120 °C for 24 h. The reaction mixture was cooled to r.t. and filtered through a short Celite pad and washed with CH2Cl2 several times. The filtrate was concentrated by vacuum and purified on a silica gel column using hexane/EtOAc as eluent to give the corresponding pure phenanthridone product 6.

Reference： [1]Gandeepan, Parthasarathy; Rajamalli, Pachaiyappan; Cheng, Chien-Hong [Synthesis, 2016, vol. 48, # 12, p. 1872 - 1879]

51
[ 64-19-7 ]
[ 371-40-4 ]
[ 351-83-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine In dichloromethane at 0 - 25℃; for 1h;
86%	With 1-methyl-3-(4-sulfonylbutyl)-1H-imidazol-3-ium trifluoromethanesulfonate at 90℃; for 0.166667h; Microwave irradiation; chemoselective reaction;	Typical procedure for N-acylation Amines (microwave irradiation): General procedure: A mixture of amines (0.01 mol), acetic acid (0.015 mol, 1 mL) and [BMIM(SO3H)][OTf] (50 mol %) was introduced into a Biotage microwave oven and heated for 6 to 9 minutes at 90oC. Progress of the reaction was monitored by TLC and GC-MS. After completion of reaction, the reaction mass was cooled at room temperature and poured into ice water. The crystals of N-acylated product so obtained were filtered, washed with of cold ethanol-water mixture (10-15mL) and dried.
82%	With palladium (II) nanoparticles supported on Schiff-base modified clinoptilolite nanocatalyst In neat (no solvent) at 20℃; for 0.333333h; Green chemistry; chemoselective reaction;	2.4 General procedure for N-acylation of amines General procedure: Pd(at)MCP (0.012g) was added to a mixture of amine (1mmol) and acetic acid (1.2mmol) and the whole mixture was stirred in a round bottomed flask at room temperature for the appropriate time (Table 3). The reaction progress was followed by GC and TLC (eluent, n-hexane:ethyl acetate, 4:1). After completion of the reaction, EtOAc (10mL) was added to the reaction mixture, and the resulting mixture filtered. The filtrate was washed with 1M HCl (3×5mL) and then the organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuum to obtain pure N-acylated products.

72%	In ethyl acetate at 110℃;	Method II. Compound 3a was synthesized using a modified procedure.2 To a solution of substituted aniline (1.0 equiv.) in EtOAc was added acetic acid (5.0 equiv.). The mixture was refluxed at 110 C overnight then cooled to room temperature. After the crude mixture was concentrated in vacuo, the resulting solid was recrystallized in EtOAc/hexanes. The solid was collected and washed with hexanes to give the product.
	With 2,6-dimethylpyridine; 1,2,2,3,4,4-hexamethylphosphetane 1-oxide; 4-Phenylpyridine 1-oxide; diethyl bromomethylmalonate; diphenylsilane In acetonitrile at 40℃; for 6h; Sealed tube; Inert atmosphere;

Reference： [1]Brindisi, Margherita; Brogi, Simone; Maramai, Samuele; Grillo, Alessandro; Borrelli, Giuseppe; Butini, Stefania; Novellino, Ettore; Allarà, Marco; Ligresti, Alessia; Campiani, Giuseppe; Di Marzo, Vincenzo; Gemma, Sandra [RSC Advances, 2016, vol. 6, # 69, p. 64651 - 64664]
[2]Savanur, Hemantkumar M.; Malunavar, Shruti S.; Prabhala, Pavankumar; Sutar, Suraj M.; Kalkhambkar, Rajesh G.; Laali, Kenneth K. [Tetrahedron Letters, 2019, vol. 60, # 42]
[3]Amirsoleimani, Mina; Khalilzadeh, Mohammad A.; Zareyee, Daryoush [Journal of Molecular Structure, 2021, vol. 1225]
[4]Lasing, Thitiya; Phumee, Atchara; Siriyasatien, Padet; Chitchak, Kantima; Vanalabhpatana, Parichatr; Mak, Kit-Kay; Hee Ng, Chew; Vilaivan, Tirayut; Khotavivattana, Tanatorn [Bioorganic and Medicinal Chemistry, 2020, vol. 28, # 1]
[5]Lipshultz, Jeffrey M.; Radosevich, Alexander T. [Journal of the American Chemical Society, 2021, vol. 143, # 36, p. 14487 - 14494]

52
[ 351-83-7 ]
[ 399-35-9 ]

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 4748 - 4753
[2]Organic Letters,2021,vol. 23,p. 3015 - 3020
[3]Angewandte Chemie - International Edition,2019,vol. 58,p. 4566 - 4570
Angew. Chem.,2019,vol. 58,p. 4566 - 4570,5
[4]Chemistry - A European Journal,2017,vol. 23,p. 7031 - 7036

53
[ 351-83-7 ]
[ 1009-22-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	With NBS In acetonitrile for 2h; Irradiation; regioselective reaction;
89%	With NBS; silver hexafluoroantimonate; copper (II) acetate; [Cp^A₅RhCl₂]₂ In 1,2-dichloro-ethane at 20℃; for 18h; Schlenk technique; Inert atmosphere; regioselective reaction;
87%	With NBS; bis[dichlorido(η⁵-1,2,3,4,5-pentamethyl-cyclopentadienyl)iridium(III)]; <i>N</i>-<i>tert</i>-butoxycarbonyl-<i>L</i>-phenylalanine; silver(I) bis(trifluoromethanesulfonyl)imide In 1,2-dichloro-ethane at 20℃; for 4h; Inert atmosphere; Sealed tube;

87%	With acetic anhydride; copper(II) bis(trifluoromethanesulfonate); N-(benzenesulfonyl)-N-fluorobenzenesulfonamide; sodium bromide In acetonitrile at 80℃; Inert atmosphere; regioselective reaction;
79%	With NBS; methanesulfonic acid; NiCl₂·6H₂O In lithium hydroxide monohydrate at 20℃; for 5h; Sealed tube; Microwave irradiation; Green chemistry; regioselective reaction;	Procedure B General procedure: A 10 mL microwave vial was charged with an anilide or carbamate derivative (1.0 equiv, 0.5 mmol), NXS (1.2 equiv, 0.6 mmol), Ag2CO3 (10 mol%, 14 mg), MSA (3.0 equiv, 1.5 mmol, 144 mg) and toluene (2.0 mL). The vial was then sealed and stirred at 50 °C, for 8 h. After the reaction time, the mixture was diluted with EtOAc and washed with sodium bicarbonate solution. The organic layer was dried with anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (n-hexane/EtOAc) to give the desired product.
633 kg	With bromine at 10 - 15℃; for 3h; Large scale;	1.4; 2.4 (4) Put 1600kg of compound C into the reactor, cool down to 10-15°C, add 400kg of bromine dropwise, pay attention to the absorption of exhaust gas during the dropwise addition, keep the reaction for 3h after the dropwise addition, add 500kg of water, stir, stand for stratification, The organic layer was washed with an aqueous solution of sodium bisulfite, allowed to stand, and the layers were separated. The dichloromethane layer was concentrated to substantially no fractions, 1700 kg of methanol was added, the temperature was increased to dissolve, the temperature was lowered to 0-5 °C for crystallization for 1 h, suction filtration, centrifugation, and drying. 633kg of o-bromo-p-fluoroacetylaniline was obtained by drying, and the purity was 98.8%.

Reference： [1]Singh, Harshvardhan; Sen, Chiranjit; Sahoo, Tapan; Ghosh, Subhash Chandra [European Journal of Organic Chemistry, 2018, vol. 2018, # 34, p. 4748 - 4753]
[2]Tanaka, Jin; Shibata, Yu; Joseph, Anton; Nogami, Juntaro; Terasawa, Jyunichi; Yoshimura, Ryo; Tanaka, Ken [Chemistry - A European Journal, 2020, vol. 26, # 26, p. 5774 - 5779]
[3]Kathiravan, Subban; Nicholls, Ian A. [Chemistry - A European Journal, 2017, vol. 23, # 29, p. 7031 - 7036]
[4]Jin, Lianwen; Zeng, Xiaoli; Li, Siyang; Qiu, Guofu; Liu, Peng [European Journal of Organic Chemistry, 2022, vol. 2022, # 24]
[5]Kianmehr, Ebrahim; Afaridoun, Hadi [Synthesis, 2021, vol. 53, # 8, p. 1513 - 1523]
[6]Current Patent Assignee: NINGXIA GINSENG PHARMACEUTICAL INDUSTRY LTD - CN114163346, 2022, A Location in patent: Paragraph 0009-0012

54
[ 351-83-7 ]
[ 40339-20-6 ]
C₁₈H₁₆FNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With silver hexafluoroantimonate; copper(II) acetate dihydrate; C₂₂H₃₀Co₂I₂O₂; silver carbonate In nitromethane at 80℃; for 15h; Inert atmosphere;

Reference： [1]Kuppusamy, Ramajayam; Santhoshkumar, Rajagopal; Boobalan, Ramadoss; Wu, Hsin-Ru; Cheng, Chien-Hong [ACS Catalysis, 2018, vol. 8, # 3, p. 1880 - 1883]

55
[ 351-83-7 ]
[ 1009-22-9 ]
[ 392-14-3 ]

Yield	Reaction Conditions	Operation in experiment
56%	With N-Bromosuccinimide; cobalt acetylacetonate; trifluoroacetic acid; silver(l) oxide In 1,2-dichloro-ethane at 60℃; for 16h; Overall yield = 70 %; regioselective reaction;

Reference： [1]Li, Ze-lin; Sun, Kang-kang; Cai, Chun [Organic and Biomolecular Chemistry, 2018, vol. 16, # 30, p. 5433 - 5440]

56
[ 351-83-7 ]
[ 98-80-6 ]
[ 13024-31-2 ]

Yield	Reaction Conditions	Operation in experiment
61%	With ammonium cerium (IV) nitrate; caesium carbonate In acetonitrile at 20℃; for 40h; Sealed tube; Irradiation;	2 In an 8 ml reaction tube, a magneton, 4-fluoroacetanilide (0.3 mmol), and phenylboric acid (0.6 mmol) were sequentially added.Ammonium cerium nitrate (0.9 mmol), cesium carbonate (0.45), and acetonitrile (3 mL) were reacted.After the reaction tube was sealed, the reaction mixture was bubbled with nitrogen for 10 minutes, and then stirred at room temperature for 40 hours with 36 W of blue light.The reaction solution was extracted with EtOAc, washed with EtOAc and evaporated.The product was isolated by column chromatography (yield 61%).

Reference： [1]Current Patent Assignee: SHAOXING UNIVERSITY - CN109232289, 2019, A Location in patent: Paragraph 0028-0030

57
[ 1374152-38-1 ]
[ 351-83-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	With dipotassium peroxodisulfate; sodium triflate In acetonitrile at 80℃; for 3h;	7-9 Example 7 0.3 mmol of 4-fluoro-α-azido-styrene,0.03 mmol of sodium triflate,0.3mmol potassium persulfate was added to a 15mL thick-wall pressure-resistant reaction tube.Further, 3 mL of acetonitrile was added as a solvent. then,The magnetic stirring was carried out at 80 ° C for 3 hours. After cooling to room temperature,Add two spoons of column chromatography silica gel (100-200 mesh) to the reaction solution.And removing the solvent by distillation under reduced pressure.The product pure N-(4-fluorophenyl)acetamide (using petroleum ether / ethyl acetate = 5:1 as eluent) was obtained by column chromatography. This material was a yellow-white solid with a yield of 70%.

Reference： [1]Current Patent Assignee: ZHEJIANG UNIVERSITY OF TECHNOLOGY - CN109422662, 2019, A Location in patent: Paragraph 0048-0059

58
[ 351-83-7 ]
[ 103-84-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	With 2-methyl-propan-1-ol; methanesulfonato(2-dicyclohexylphosphino -2’,6’-di-i-propoxy-1,1‘-biphenyl)(2’-amino-1,1’-biphenyl-2-yl)palladium(II); sodium tert-pentoxide In toluene at 80℃; for 48h; Sealed tube; Inert atmosphere;
81%	With (2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1‘-biphenyl)[2-(2’-methylamino-1,1’-biphenyl)]palladium(II) methanesulfonate; sodium tert-pentoxide; isopropyl alcohol In toluene at 80℃; Inert atmosphere;
82 %Spectr.	With N,N,N',N'-tetramethyl-para-phenylenediamine In 1-methyl-pyrrolidin-2-one at 20℃; for 4h; UV-irradiation;

Reference： [1]Gair, Joseph J.; Grey, Ronald L.; Giroux, Simon; Brodney, Michael A. [Organic Letters, 2019, vol. 21, # 7, p. 2482 - 2487]
[2]Brodney, Michael A.; Gair, Joseph J.; Giroux, Simon; Grey, Ronald L. [Organic Syntheses, 2021, vol. 98, p. 131 - 146]
[3]Toriumi, Naoyuki; Yamashita, Kazuya; Iwasawa, Nobuharu [Chemistry - A European Journal, 2021, vol. 27, # 49, p. 12635 - 12641]

59
[ 351-83-7 ]
[ 405-67-4 ]
[ 371-40-4 ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3800 - 3806

60
[ 17431-03-7 ]
[ 351-83-7 ]
(S)-ethyl 2-(4-acetamidophenylamino)-3-methylbutanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate In 1,2-dichloro-ethane at 25℃; for 72h; Irradiation; Inert atmosphere;	37 Example 37 N-(4-fluorophenyl)acetamide a20 (0.0153 g, 0.10 mmol), acridine photosensitizer (A) (0.0046 g, 0.008 mmol) and L-valine ethyl ester b1 were added sequentially under argon atmosphere. (0.0218 g, 0.15 mmol), 1,2-dichloroethane (DCE) 2.0 mL.The reaction was irradiated for 72 h at room temperature under a 6 W blue light lamp.After completion of the reaction, the solvent was evaporated under reduced pressure and purified by column chromatography, eluent: (V) petroleum ether / (V) ethyl acetate = 2/1.Yellow liquid (37) (0.0158 g, 97%) was obtained.
57%	With 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate In 1,2-dichloro-ethane at 50℃; for 72h; Inert atmosphere; Irradiation; Schlenk technique;

Reference： [1]Current Patent Assignee: CENTRAL CHINA NORMAL UNIVERSITY - CN110294685, 2019, A Location in patent: Paragraph 0171-0174
[2]Shi, Weimin; Zhang, Jingjie; Zhao, Fengqian; Wei, Wei; Liang, Fang; Zhang, Yin; Zhou, Shaolin [Chemistry - A European Journal, 2020, vol. 26, # 65, p. 14823 - 14827]

61
[ 371-40-4 ]
[ 507-09-5 ]
[ 351-83-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	In lithium hydroxide monohydrate at 20℃; for 12h;	4 Example 4 Under room temperature and air atmosphere, 4-fluoroaniline (0.3 mmol), thioacetic acid (0.45 mmol), and water solvent (H2O) (1 mL) were successively added to the reaction tube, and then the reaction was performed at room temperature for 12 hours. Column chromatography gave the product in 90% yield.
73%	With 9-mesityl-10-methylacridin-10-ium tetrafluoroborate In acetonitrile at 20℃; for 5h; Irradiation;
73%	With 9-mesityl-10-methylacridin-10-ium tetrafluoroborate In acetonitrile at 20℃; for 5h; Irradiation;	5 Example 5: Preparation of N- (4-fluorophenyl) acetamide (3e) In air, p-fluoroaniline (0.2 mmol, 23 mg) was dissolved in acetonitrile (2 mL), and Mes-Acr-MeBF4 (2 mol%, 2 mg) and thioacetic acid (0.4 mmol, 30 mg) were added. The mixture was stirred for 5 hours at room temperature under a 36W blue LED. The mixture was quenched with water (2 mL) and then extracted with EtOAc (3 x 4 mL). The organic phase was washed with brine, dried over Na 2 SO 4 and spin-dried, and then separated by column chromatography to obtain 22 mg of a white solid product with a yield of 73%.

Reference： [1]Current Patent Assignee: WENZHOU UNIVERSITY - CN113979885, 2022, A Location in patent: Paragraph 0059-0062
[2]Song, Wangze; Dong, Kun; Li, Ming [Organic Letters, 2020, vol. 22, # 2, p. 371 - 375]
[3]Current Patent Assignee: DALIAN UNIVERSITY OF TECHNOLOGY - CN110698360, 2020, A Location in patent: Paragraph 0035-0038

62
[ 351-83-7 ]
[ 877-90-7 ]
[ 36556-53-3 ]
[ 398-91-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 37% 2: 10% 3: 44%	With hydrogen fluoride; antimony pentafluoride; sodium chloride at -20℃; for 2h;

Reference： [1]Mamontov, Alexander; Martin-Mingot, Agnès; Métayer, Benoit; Karam, Omar; Zunino, Fabien; Bouazza, Fodil; Thibaudeau, Sébastien [Chemistry - A European Journal, 2020, vol. 26, # 46, p. 10411 - 10416]

63
[ 75-05-8 ]
[ 371-40-4 ]
[ 351-83-7 ]

Yield	Reaction Conditions	Operation in experiment
66%	With tert.-butylnitrite; trifluorormethanesulfonic acid; water at 60℃; for 24h;	2. General procedure for the synthesis of acetamide General procedure: To a stirred solution of amine (1.0 mmol) in CH3CN (5.0 mL) was addedt-BuONO (1.5 mmol, 1.5 equiv), CF3SO3H (1.5 mmol, 1.5 equiv) and H2O (5.0 mmol,5.0 equiv). The reaction mixture was stirred under an atmosphere of air at 60 oC for24 h. After the reaction was complete, the reaction mixture was purified by flashchromatography on silica gel with a mixture of petroleum ether and ethyl acetate aseluent.

Reference： [1]Duan, Pan; Guo, Yu; Kang, Huan; Li, Yi-Na; Wen, Xianghao; Xiao, Fang; Zeng, Yao-Fu; Zhang, Na-Na [Synlett, 2019, vol. 30, # 19, p. 2169 - 2172]

64
[ 92-86-4 ]
[ 351-83-7 ]
C₂₈H₂₂F₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67.83%	With copper(l) iodide; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 140 - 142℃; Inert atmosphere; Dean-Stark;	2 Put 61.2g N-acetyl-4-fluoroaniline, 31g 4,4'-dibromobiphenyl, 38g CuI, 1.2L xylene and 48.05g t-BuONa into a 2L three-necked flask, install heating stirring, thermometer, spherical Condenser, water separator and nitrogen protection device. Fill with nitrogen for about 10 times, and slowly heat to reflux under the protection of nitrogen. During the reflux process, the low boiling point tert-butanol is continuously separated, keep the temperature of the reaction liquid at 140-142, reflux for 24-32h, take a sample and check the GC, 4,4'-dibromobiphenyl content <0.5%, monobromo content <0.2%, the reaction can be terminated. After filtration, quenching, water washing, drying, column chromatography, desolvation, and toluene recrystallization, 30.94g of I-2b-2 is obtained, and the yield is 67.83%.

Reference： [1]Current Patent Assignee: SHANDONG SHENGHUA NEW MATERIAL TECHNOLOGY CO LTD - CN111848542, 2020, A Location in patent: Paragraph 0019

65
[ 405-99-2 ]
[ 75-36-5 ]
[ 351-83-7 ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: para-fluorostyrene With methanesulfonic acid; trimethylsilylazide In tetrachloromethane at 80℃; for 4h; Stage #2: acetyl chloride With triethylamine In dichloromethane at 20℃; for 6h;	4 Example 4 N-(4-fluorophenyl)acetamide Take a reaction tube, add 86 mg of trimethylsilane azide, 36.6 mg of p-fluorostyrene, 576 mg of methanesulfonic acid, and 1.0 mL of carbon tetrachloride, and stir at 80°C for 4 hours. After the reaction, the reaction was quenched by adding 10 mL of sodium hydroxide solution, extracted with ethyl acetate 3 times, the organic phase was washed with 5 mL of brine, and the organic phases were combined. After concentration, 35.3 mg of acetyl chloride, 45.5 mg of triethylamine, and 5 mL of dichloromethane were added. After stirring for 6 hours at room temperature, after concentration, column chromatography obtains 32 mg of N-(4-fluorophenyl)acetamide with a yield of 63%

Reference： [1]Current Patent Assignee: PEKING UNIVERSITY - CN112321436, 2021, A Location in patent: Paragraph 0141-0143

66
[ 459-47-2 ]
[ 351-83-7 ]

Reference： [1]Science,2020,vol. 367,p. 281 - 285

67
[ 351-83-7 ]
[ 106-45-6 ]
N-[4-fluoro-2-(p-tolylthio)phenyl]acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium peroxodisulfate; methanesulfonic acid; NiCl₂·6H₂O In 1,2-dichloro-ethane at 140℃; for 24h; Sealed tube;	Thiolated Compounds 3 and 4; General Procedure General procedure: A reaction vessel (micro vial, 10 mL) was charged with an anilide 1 (0.2 mmol, 1.0 equiv), a thiol 2 (0.4 mmol, 2.0 equiv), NiCl2·6H2O (0.04 mmol, 20 mol%), K2S2O8 (0.4 mmol, 2.0 equiv), CH3SO3H (0.1 mmol, 0.5 equiv), and DCE (1.5 mL). The reaction vessel was sealed and the contents were stirred at 140 °C for 24 h. After cooling to r.t., the reaction mixture was diluted with H2O (20 mL) and extracted with EtOAc (3 × 10 mL). The combined extracts were washed with aq NaHCO3 and dried (Na2SO4). After evaporation of the solvent, the crude product was purified by column chromatography on silica gel (PE/EtOAc 6:1).

Reference： [1]Kianmehr, Ebrahim; Doraghi, Fatemeh; Foroumadi, Alireza [Synthesis, 2022, vol. 54, # 10, p. 2464 - 2472]

68
[ 431-03-8 ]
[ 371-40-4 ]
[ 351-83-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	In ethanol at 20℃; for 6h; Schlenk technique; Irradiation; Green chemistry;	3 Example 3 In a 25 mL Schlenk tube, amine 1c (0.2 mmol, 22.2 mg), 2,3-butanedione (1.2 mmol, 103.3 mg), ethanol (95%, 0.5 mL) were added sequentially in a 25 mL Schlenk tube, and then after 6 hours of conventional stirring under 40W white LED irradiation, the reaction system was quenched with saturated sodium sulfite solution, extracted with ethyl acetate 3 times, combined with the organic layer, and dried with anhydrous sodium sulfate. The solvent and silica gel adsorption are removed by rotary evaporator, and the product 3c can be obtained by simple column chromatography, and the yield is 83%. The main test data of the prepared products are as follows, and through the analysis, it can be seen that the actual synthetic products are consistent with the theoretical analysis.

Reference： [1]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN113717071, 2021, A Location in patent: Paragraph 0018-0019

69
3-methyl-5H-1,4,2-dioxazol-5-one [ No CAS ]
[ 448-59-9 ]
[ 351-83-7 ]

Yield	Reaction Conditions	Operation in experiment
97%	With dichloromethane at 30℃; for 12h; Sealed tube; Irradiation; Glovebox; Inert atmosphere;

Reference： [1]Chang, Sukbok; Jung, Hoimin; Kim, Dongwook; Kweon, Jeonguk; Seo, Sangwon; Zhou, Zijun [Journal of the American Chemical Society, 2022]

70
[ 350-46-9 ]
[ 507-09-5 ]
[ 351-83-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	With NH₄HCO₃ In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Irradiation;	7 Example 7 A one-pot reductive acylation method of light-induced nitro compounds, comprising the following steps:The nitro compound, thiocarboxylic acid, ammonium bicarbonate, and tetrahydrofuran solvent were added to the reaction vessel, and under nitrogen protection, irradiated with an LED lamp, and reacted at room temperature for 12 hours. That is, the corresponding amide compound is obtained. The yield was 84% with:The molar ratio of nitro compound, thiocarboxylic acid and ammonium bicarbonate is 1:4:2;The consumption of organic solvent is 5mL/mmol in molar amount of nitro compound;The structural formula of the nitro compound is R1-NO2, wherein R1 is 4-fluorophenyl.The structural formula of thiocarboxylic acid is R2COSH, wherein R2 is methyl.Further, the LED light is a purple LED light with a wavelength of 390 nm.Further, the post-processing is dichloromethane extraction and magnesium sulfate drying.Further, the concrete steps of silica gel chromatographic column purification are:Column packing;sample;Elution with ethyl acetate/petroleum ether eluent.

Reference： [1]Current Patent Assignee: WENZHOU UNIVERSITY - CN113956174, 2022, A Location in patent: Paragraph 0142-0157

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	351-83-7	MDL No. :	MFCD00016335
Formula :	C₈H₈FNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JHEFOJNPLXSWNZ-UHFFFAOYSA-N
M.W :	153.15	Pubchem ID :	9601
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 351-83-7 ] {[proInfo.proName]}

Quality Control of [ 351-83-7 ]

Related Doc. of [ 351-83-7 ]

Product Details of [ 351-83-7 ]

Safety of [ 351-83-7 ]

Application In Synthesis of [ 351-83-7 ]

[ 351-83-7 ] Synthesis Path-Upstream 1~14

[ 351-83-7 ] Synthesis Path-Downstream 1~70

Related Functional Groups of
[ 351-83-7 ]

Fluorinated Building Blocks

Aryls

Amides

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

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