Name: 1450-74-4|1-(5-Chloro-2-hydroxyphenyl)ethanone|98%
Brand: Ambeed
SKU: A113905
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1
[ 876-27-7 ]
[ 1450-74-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	With hydrogen fluoride supported on silica gel In neat (no solvent) at 55℃; for 4h; Green chemistry;	3.4. General Procedure for Synthesis of Hydroxyaryl Ketones General procedure: A mixture of aryl ester (25 mmol), HFSiO2 (2 g), and EtOAc (5 mL) was charged in a 50 ml flask and stirred for 5min. EtOAc was used for homogenization of the reactionmixture in this step. The solvent was evaporated under vacuumand the residue was heated with the classical method for 4 h at 55°C for aryl acetates and at 75°C for aryl benzoates(Table 1). After cooling, the reaction mixture was extractedwith EtOAc (3 × 10 mL) and the solvent was removed under vacuum. The residue was subjected to short column chromatography (EtOAc/hexane; 1:5) on silica gel to obtain pureproducts. All the isolated hydroxyaryl ketones successfullygave the related spectral data of IR, 1H NMR, 13C NMR andMS spectrometers (see the Supporting Information, Fig. 12S-39S) and comparison with authentic samples prepared byreported methods [33-36].
90%	With aluminum (III) chloride In neat (no solvent) at 140 - 150℃;	Synthesis of 2-hydroxy-5-chloroacetophenone 3c p-Chlorophenyl acetate 2c (10 gm, 0.091mol) was in 500 mL round bottom flask containing aluminium chloride (14.56 gm, 0.11 mol). It was heated on an oil bath at 140-150 °C for 5-6 hr. The progress of the reaction was monitored by TLC using ethyl acetate:hexane as a solvent system. The reaction mixture was quenched with crushed ice and obtained solid product was extracted with ethyl acetate (2×50 mL). The organic extracts were washed with brine solution (2×15 mL) and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure to afford the corresponding crude compound. The obtained crude compound 3c was recrystallized using aq. ethanol. Yield 90%. M.p. 54-56 °C.
88%	With potassium carbonate In hexane at 25℃; for 12h; Irradiation;

87%	With trifluorormethanesulfonic acid at 0 - 20℃; for 16h; regiospecific reaction;	4.4. General procedure of Fries rearrangement for O-acyloxy benzenes in TfOH General procedure: O-Acyloxy benzenes (0.28 mmol) were dissolved in TfOH (3 ml) at 0 °C. The reaction mixture was warmed to room temperature for appropriate time in Table 3, then poured into cold water and ethyl acetate. The organic layer was washed with 1 M HCl, saturated NaHCO3, and saturated NaCl, and dried over MgSO4, then filtrated. The filtrate was concentrated and the residue was subjected silica column chromatography to afford acylated products. All spectral data were identical with the literatures.26
85%	With aluminium trichloride In chlorobenzene for 0.0333333h; Irradiation;
82%	With aluminum (III) chloride at 120 - 160℃; for 30h;
79%	With N,N-dimethyl-formamide; zinc at 68℃; for 18h; microwave irradiation;
74.14%	With aluminium trichloride at 140℃; for 2h;
62%	With aluminium trichloride at 160℃; for 1h;
60%	With aluminum (III) chloride at 120 - 160℃;	5'-chloro-2'-hydroxyacetophenone (3): 4-chlorophenyl acetate (2) (0.1 mole) and anhydrous aluminum trichloride (0.11 mole) were mixed thoroughly in a round bottom flask. The reaction mixture was heated gradually at 120°C till HCl gas was completely exhausted. The heating was extended for 2 hours at 160°C. The progress and completion of the reaction was monitored by TLC. At the end of the reaction the resulting aluminum complex was decomposed from crushed ice containing little amount of hydrochloric acid. The crude product was filtered dried and crystallized from methanol. Yield 60%, m. p. 53-55 °C (Reported m.p. 53°C).
55%	With aluminium trichloride at 120℃;
	With aluminium trichloride at 120℃;
	With aluminium trichloride at 130℃;
	With boron trifluoride at 125℃; unter Druck;
	With aluminium trichloride at 175 - 185℃;
	With aluminium trichloride
	With Lewis acid In nitrobenzene Heating;
72 g	With aluminium trichloride at 160℃; for 2h;
	With aluminium trichloride Heating;
	With aluminium trichloride Heating;
	With aluminium trichloride at 120℃;
	With aluminum (III) chloride; sodium chloride Neat (no solvent);
	With titanium tetrachloride; 1-n-butyl-3-methylimidazolim bromide at 120℃; for 3h; Inert atmosphere;
	With aluminum (III) chloride
	With aluminum (III) chloride
	Stage #1: 4-chlorophenyl acetate With aluminum (III) chloride at 120℃; for 6h; Stage #2: With water Cooling;	2 Synthesis of substituted o-hydroxyacetophenone General procedure: Powdered anhydrous AlCl3 (186 g, 1.4 mol) was added little by little to acetic acid phenyl ester b1 (95.3 g, 0.7 mol) in a round-bottomed flask in an ice-water bath. The resultant mixture was heated to 120 °C for 6 h in an oil bath. Then the reaction mixture was added a lot of crushed ice for hydrolysis. The new formed organic layer in the reaction mixture was extracted by EtOAc, dried over anhydrous Na2SO4, and filtered off by suction filtration. The solvent was removed under reduced pressure to give the crude product, which was then purified by chromatography on silica using petroleum ether/ethyl acetate as the eluent. o-hydroxyacetophenone c1 (20.1 g, 21%) was obtained
	With aluminum (III) chloride
	With aluminum (III) chloride Heating;
	With Fluoro Flash In neat (no solvent) at 80℃; for 4h; Green chemistry;	4.2 General procedure for Fries rearrangement and catalyst preparation General procedure: Catalyst (FSG) was purchased from Fluorous Technologies Inc. and used without further purification. Its synthesis procedure is reported by Curran et al. [24]. General procedure for Fries rearrangement was done by adding FSG to aryl ester at the ambient temperatures. Before adding FSG to reaction mixture, aryl esters were obtained by in situ formation through the reaction of acyl chloride derivatives and phenol derivatives. Thus, to a 100ml round bottom flask stirring by a magnetic bar 10mmol of phenols was added and then, 10mmol of acyl chloride derivatives (for catechols 20mmol) was added dropwise and allowed to react at room temperature. After 30min, temperature was raised to remove HCl from reaction mixture. Then 1g of FSG was added to reaction mixture at ambient temperature. After 4h heating at appropriate temperature in oil bath, the reaction mixture was cooled to room temperature and washed with dichloromethane. The catalyst was separated by filtration. The solvent was removed by rotary evaporator and resulting mixture was separated by column chromatography (stationary phase: silica-gel, eluent:hexane:ethyl acetate) and purified by recrystallization. All isolated products successfully gave related spectral data of IR, NMR, and mass spectrometers.
	With aluminum (III) chloride at 120℃;
	With aluminum (III) chloride at 120 - 130℃; Dean-Stark;
	With aluminum (III) chloride at 120 - 130℃;
	With aluminum (III) chloride at 150℃;
	With aluminum (III) chloride
	With aluminum (III) chloride at 80 - 150℃; for 3h; Enzymatic reaction;	4.1.2. Synthesis of 1-(5-chloro-2-hydroxyphenyl)propan-1-one(11a) General procedure: A mixture of 10a (6.5 g, 35.20 mmol) and AlCl3 (14.07 g,105.60 mmol) was heated at 80 C for 1 h then at 150 °C for 2 h theresulting residuewas decomposed with 3 N HCl and extracted withEtOAc. The organic layer was washed with brine, dried over MgSO4,and evaporated under reduced pressure to give crude productwhich was purified by flash chromatography on silica gel using amixture of EtOAc, hexanes (1:30) as eluent to yield 11a (5 g, 77%) aswhite solid
	With aluminum (III) chloride at 120℃; for 5h;	2.1.2.2. Fries Rearrangement of Ester Derivatives General procedure: The above reaction mixture was treated with anhydrousAluminum Chloride (AlCl3) (28.03 g, 0.2100 moles) at120oC for 5 hours. The reaction was monitored by TLC(Ethylacetate:hexane::30:70). The reaction was cooled downand neutralized by ammonium chloride. The mixture wasextracted with ethyl acetate (3 x 250 ml). All the ethyl acetatefractions were combined and concentrated after treatingwith sodium sulfate (100 g) to obtain the crude product(Scheme 1).
	With aluminum (III) chloride at 0 - 120℃; for 5h;
	With aluminum (III) chloride
	With aluminum (III) chloride at 120℃;

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[2]Shaikh, Mubarak H.; Subhedar, Dnyaneshwar D.; Khedkar, Vijay M.; Jha, Prakash C.; Khan, Firoz A. Kalam; Sangshetti, Jaiprakash N.; Shingate, Bapurao B. [Chinese Chemical Letters, 2016, vol. 27, # 7, p. 1058 - 1063]
[3]Garcia, Hermenegildo; Primo, Jaime; Miranda, Miguel Angel [Synthesis, 1985, # 9, p. 901 - 902]
[4]Location in patent: experimental part Murashige, Ryo; Hayashi, Yuka; Ohmori, Syo; Torii, Ayuko; Aizu, Yoko; Muto, Yasuyuki; Murai, Yuta; Oda, Yuji; Hashimoto, Makoto [Tetrahedron, 2011, vol. 67, # 3, p. 641 - 649]
[5]Sridar, V.; Rao, V. S. Sundara [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 2, p. 184 - 185]
[6]Basawaraj, Raga; Gahininath, Wadikar; Chillargi, Neelavati; Alvi, Shah Nadeemuddin; Zaheeruddin [Indian Journal of Heterocyclic Chemistry, 2011, vol. 21, # 2, p. 151 - 156]
[7]Paul, Satya; Gupta, Monika [Synthesis, 2004, # 11, p. 1789 - 1792]
[8]Akamanchi; Padmawar; Thatte; Rege; Dahanukar [Pharmacy and Pharmacology Communications, 1999, vol. 5, # 5, p. 323 - 329]
[9]Wu, Shao-Yong; Hirashima, Akinori; Kuwano, Eiichi; Eto, Morifusa [Agricultural and Biological Chemistry, 1987, vol. 51, # 2, p. 537 - 548]
[10]Upadhyay, Kuldip; Bavishi, Abhay; Thakrar, Shailesh; Radadiya, Ashish; Vala, Hardevsinh; Parekh, Shrey; Bhavsar, Dhairya; Savant, Mahesh; Parmar, Manisha; Adlakha, Priti; Shah, Anamik [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 8, p. 2547 - 2549]
[11]Gabriel, Gabriel; Pickles, Robert; Tyman, John H. P. [Journal of Chemical Research, Miniprint, 1989, # 11, p. 2713 - 2739]
[12]Wittig [Chemische Berichte, 1924, vol. 57, p. 92][Justus Liebigs Annalen der Chemie, 1926, vol. 446, p. 157 Anm. 2, 177] v. Auwers; Wittig [Chemische Berichte, 1924, vol. 57, p. 1273]
[13]Sen; Bhargava [Journal of the Indian Chemical Society, 1949, vol. 26, p. 366,367]
[14]Kindler; Oelschlaeger [Chemische Berichte, 1954, vol. 87, p. 194,201]
[15]Dandegaonker,S.H.; Shet,S.G. [Monatshefte fur Chemie, 1965, vol. 96, p. 1214 - 1223]
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[18]Sebille, Sophie; De Tullio, Pascal; Becker, Bénédicte; Antoine, Marie-Hélène; Boverie, Stéphane; Pirotte, Bernard; Lebrun, Philippe [Journal of Medicinal Chemistry, 2005, vol. 48, # 2, p. 614 - 621]
[19]Ishar; Singh, Gurpinder; Singh, Satyajit; Sreenivasan; Singh, Gurmit [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 5, p. 1366 - 1370]
[20]Doble, Mukesh; Karthikeyan; Padmaswar; Akamanchi [Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 21, p. 5996 - 6001]
[21]Bala, Ritu; Kumar, Rupesh; Yusuf, Mohamad; Bansal [Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 2007, vol. 46, # 9, p. 1440 - 1444]
[22]Location in patent: scheme or table Liu, Huachen; Dong, Aijun; Gao, Chunmei; Tan, Chunyan; Xie, Zhenhua; Zu, Xuyu; Qu, Long; Jiang, Yuyang [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 17, p. 6322 - 6328]
[23]Location in patent: experimental part Katkevica; Zicmanis; Mekss [Chemistry of Heterocyclic Compounds, 2010, vol. 46, # 2, p. 158 - 169]
[24]Location in patent: body text Sharma, Vinay Prabha; Kumar, Praveen; Sharma, Meenakshi [Asian Journal of Chemistry, 2011, vol. 23, # 10, p. 4616 - 4620]
[25]Location in patent: scheme or table Kelode; Mandlik; Aswar [Oriental Journal of Chemistry, 2011, vol. 27, # 3, p. 1053 - 1062]
[26]Location in patent: experimental part Petrov; Iekhlev; Teplyakov; Androsov [Russian Journal of Organic Chemistry, 2012, vol. 48, # 5, p. 728 - 735]
[27]Tu, Qi-Dong; Li, Ding; Sun, Yao; Han, Xin-Ya; Yi, Fan; Sha, Yibamu; Ren, Yan-Liang; Ding, Ming-Wu; Feng, Ling-Ling; Wan, Jian [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 11, p. 2826 - 2831]
[28]Siddiqui, Naqui-Jahan; Idrees, Mohammad; Khati, Niraj T.; Dhonde, Madhukar G. [Bulletin of the Chemical Society of Ethiopia, 2013, vol. 27, # 1, p. 85 - 94]
[29]Singh, Satyajit; Baviskar, Ashish Triambak; Jain, Vaibhav; Mishra, Nidhi; Chand Banerjee, Uttam; Bharatam, Prasad V.; Tikoo, Kulbhushan; Singh Ishar, Mohan Paul [MedChemComm, 2013, vol. 4, # 9, p. 1257 - 1266]
[30]Ghaffarzadeh, Mohammad; Ahmadi, Maryam [Journal of Fluorine Chemistry, 2014, vol. 160, p. 77 - 81]
[31]Zhu, Wufu; Chen, Chen; Sun, Chengyu; Xu, Shan; Wu, Chunjiang; Lei, Fei; Xia, Hui; Tu, Qidong; Zheng, Pengwu [European Journal of Medicinal Chemistry, 2015, vol. 93, p. 64 - 73]
[32]Bano, Mohsina; Barot, Kuldipsinh P.; Jain, Shailesh V.; Ghate, Manjunath D. [Medicinal Chemistry Research, 2015, vol. 24, # 7, p. 3008 - 3020]
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[34]Dofe, Vidya S.; Sarkate, Aniket P.; Kathwate, Santosh H.; Gill, Charansingh H. [Heterocyclic Communications, 2017, vol. 23, # 4, p. 325 - 330] Dofe, Vidya S.; Sarkate, Aniket P.; Shaikh, Zarina M.; Gill, Charansingh H. [Heterocyclic Communications, 2018, vol. 24, # 1, p. 59 - 65]
[35]Kolhe, Nitin H.; Jadhav, Shridhar S. [Research on Chemical Intermediates, 2019, vol. 45, # 3, p. 973 - 996]
[36]Youssif, Bahaa G.M.; Mohamed, Ashraf M.; Osman, Essam Eldin A.; Abou-Ghadir, Ola F.; Elnaggar, Dina H.; Abdelrahman, Mostafa H.; Treamblu, Laurent; Gomaa, Hesham A.M. [European Journal of Medicinal Chemistry, 2019, vol. 177, p. 1 - 11]
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[41]Current Patent Assignee: JIANGXI SCIENCE & TECHNOLOGY NORMAL UNIVERSITY - CN113563321, 2021, A Location in patent: Paragraph 0021-0023

2
[ 3612-20-2 ]
[ 1450-74-4 ]
[ 81122-68-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	In methanol Heating;
86%	With pyrrolidine In methanol for 8h; Heating;
77%	With pyrrolidine In methanol at 70℃; for 3h;	i (i) 1'-Benzyl-6-chlorospiro[chromene-2,4'-piperidin]-4(3H)-one A solution of 1-(5-chloro-2-hydroxyphenyl)ethanone (1.7 g, 10 mmol), 1-benzylpiperidin-4-one (2.08 g, 11 mmol) and pyrrolidine (1.07 g, 15 mmol) in methanol (2 ml) was heated at 70 °C for 3 h. After cooling to room temperature, the reaction mixture was poured into water (20 ml), and extracted with ethyl acetate (50 ml). The organic layer was washed with 1 N aq. HCl (2 x 50 ml), 2 N aq. NaOH (50 ml), and water. Drying over Na2SO4 and evaporation of solvent afforded subtitle compound as orange-coloured oil (2.61 g, 77 %). APCI-MS: m/z 342 [M+H]+

Reference： [1]Laras, Younes; Pietrancosta, Nicolas; Moret, Vincent; Marc, Sylvain; Garino, Cedrik; Rolland, Amandine; Monnier, Valerie; Kraus, Jean-Louis [Australian Journal of Chemistry, 2006, vol. 59, # 11, p. 812 - 818]
[2]Yamato; Hashigaki; Tsutsumi; Tasaka [Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 12, p. 3494 - 3498]
[3]Current Patent Assignee: ASTRAZENECA PLC - WO2004/5295, 2004, A1 Location in patent: Page 65-66

3
[ 1450-74-4 ]
[ 105-14-6 ]
[ 70441-05-3 ]
[3-(6-Chloro-2-methyl-4-pyrrolidin-1-yl-2H-chromen-2-yl)-propyl]-diethyl-amine [ No CAS ]

Reference： [1]Angewandte Chemie,1982,vol. 94,p. 254 - 262

4
[ 1450-74-4 ]
[ 84942-40-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With nitric acid In acetic acid for 2.5h; Ambient temperature;
	With copper(II) nitrite; acetic anhydride for 1h;
	With sulfuric acid; nitric acid

Reference： [1]Burdeska, K. [Synthesis, 1982, # 11, p. 940 - 942]
[2]Bagade; Ghiya [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 1, p. 71 - 74]
[3]Location in patent: scheme or table Kelode; Mandlik; Aswar [Oriental Journal of Chemistry, 2011, vol. 27, # 3, p. 1053 - 1062]

5
[ 1450-74-4 ]
[ 80-35-3 ]
[ 77544-97-9 ]

Reference： [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 115 - 118

6
[ 1450-74-4 ]
[ 526-08-9 ]
[ 77544-99-1 ]

Reference： [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 115 - 118

7
[ 1450-74-4 ]
[ 104-88-1 ]
(E)-1-(5-chloro-2-hydroxyphenyl)-3-(4-chlorophenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium hydroxide In ethanol; water at 20℃;
79%	With sodium hydroxide In methanol; water at 20℃;
76%	With sodium hydroxide In methanol; water at 70℃;	2.1.2. Synthesis of 2′ -hydroxychalcone derivatives General procedure: Chalcones were synthesised following (Kachadourian et al., 2012),with some modifications (Scheme 2). One mL of a 50% aqueous solutionof NaOH was added to a stirred solution of each acetophenone (1 mmol)and benzaldehyde (1 mmol) in MeOH (10 mL). The reaction mixture washeated for 3-5 h at 70 C (Scheme 2) and the reaction was monitored byHPLC.Upon reaction completion, the solution was neutralized with 10%HCl(aq) and extracted twice with an equal volume of CH2Cl2. Theorganic layer was dried under reduced pressure and recrystallized fromMeOH/H2O (70/30, v/v). Compounds purity was confirmed by HPLC as>98%. These recrystallized compounds were used for chemical identificationand assays

70.6%	With potassium hydroxide In ethanol at 20℃; for 5h;
60%	With sodium hydroxide In ethanol for 48h; Ambient temperature;
	With base

Reference： [1]Sawant; Gill; Nirwan [Indian Journal of Heterocyclic Chemistry, 2012, vol. 22, # 1, p. 61 - 66]
[2]Location in patent: experimental part Aryapour, Hassan; Riazi, Gholam Hossein; Foroumadi, Alireza; Ahmadian, Shahin; Shafiee, Abbas; Karima, Oveis; Mahdavi, Majid; Emami, Saeed; Sorkhi, Maedeh; Khodadady, Sirus [Medicinal Chemistry Research, 2011, vol. 20, # 4, p. 503 - 510]
[3]Žakelj, Simon; Abin-Carriquiry, Juan Andrés; Carvalho, Diego; Colettis, Natalia; Gobec, Stanislav; Higgs, Josefina; Kamecki, Fabiola; Knez, Damijan; Marcos, Alejandra; Marcucci, Carolina; Marder, Mariel; Rademacher, Marina; de Tezanos Pinto, Felicitas [Neuropharmacology, 2021, vol. 201]
[4]Lim, Soon Sung; Jung, Sang Hoon; Ji, Jun; Shin, Kuk Hyun; Keum, Sam Rok [Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 11, p. 1786 - 1789]
[5]De Meyer; Haemers; Mishra; Pandey; Pieters; Vanden Berghe; Vlietinck [Journal of Medicinal Chemistry, 1991, vol. 34, # 2, p. 736 - 746]
[6]Zhao, Pei-Liang; Liu, Chang-Ling; Huang, Wei; Wang, Ya-Zhou; Yang, Guang-Fu [Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 14, p. 5697 - 5700]

8
[ 1450-74-4 ]
[ 874-60-2 ]
[ 88952-03-8 ]

Reference： [1]Letcher, Roy M. [Journal of Chemical Research, Miniprint, 1989, # 12, p. 2901 - 2929]

9
[ 1450-74-4 ]
[ 5629-98-1 ]
[ 15934-69-7 ]

Reference： [1]Monatshefte fur Chemie,1965,vol. 96,p. 1214 - 1223

10
[ 1450-74-4 ]
[ 77-78-1 ]
[ 6342-64-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetone for 3h; Reflux;

Reference： [1]Dalal, Aarti; Kumar, Dinesh; Kamboj, Ramesh C [Journal of the Chinese Chemical Society, 2015, vol. 62, # 12, p. 1114 - 1120]
[2]Horton,W.J.; Robertson,D.E. [Journal of Organic Chemistry, 1960, vol. 25, p. 1016 - 1020]

11
[ 1450-74-4 ]
[ 92-55-7 ]
(E)-1-(5-Chloro-2-hydroxy-phenyl)-3-(5-nitro-furan-2-yl)-propenone [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 3673 - 3681

12
[ 1450-74-4 ]
[ 74-88-4 ]
[ 6342-64-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃;	28 Combine 5'-chloro-2'-hydroxyacetophenone (17.0 g, 100 mmol) with potassium carbonate (15.1 g, 109 mmol) and iodomethane (12.5 ML, 200 mmol) in DMF and stir in a sealed vessel overnight at RT. Remove DMF and partition the residue between water and EtOAc. Dry the combined extracts over NA2S04 and concentrate. Chromatograph the resulting residue over silica gel (EtOAc/hexanes) to allow for isolation of 1- (5- Chloro-2-methoxy-phenyl) -ethanone (17.1 g, 93 %). MS (ES): (M+1) + 185.1, 187.1 M/Z. Dissolve 1- (5-CHLORO-2-METHOXY-PHENYL)-ETHANONE (8. 5 g, 46.2 mmol) in CHC13 (40 mL) and add this mixture to a warmed slurry of CuBr2 (20.6 g, 92.4 mmol) in EtOAc (150 mL). Heat the resulting mixture near reflux for approx. 3 h. Cool and filter the mixture and concentrate the resulting filtrate. Chromatograph the resulting residue over silica gel (CH2CL2) to allow for isolation of 2-bromo-1- (5-chloro-2-methoxy-phenyl)- ethanone (12.0 g, 99 %). MS (ES): (M+1) + 185. 1,187. 1 m/z.
90%	Stage #1: 5-chloro-2-hydroxyacetophenone With potassium carbonate In [⁽²⁾H₆]acetone at 23℃; for 1h; Stage #2: methyl iodide In acetone at 23℃; for 15h;	22 Intermediate 22a) A solution of 1-(5-chloro-2-hydroxyphenyl)ethanone (3.4 g) in acetone (40 mL) was added potassium carbonate (8.2 g) and the mixture was stirred at ambient temperature for 1 h. Methyl iodide (3.7 g) was added and the reaction mixture was stirred at ambient temperature for 15 h. The suspension was filtered and the volatiles were removed under reduced pressure. The residue was dissolved in Et2O and was washed with water. The organic layer was dried and the volatiles were removed under reduced pressure to yield the desired compound (90% yield).
90%	Stage #1: 5-chloro-2-hydroxyacetophenone With potassium carbonate In acetone at 20℃; for 1h; Stage #2: methyl iodide In acetone at 20℃; for 15h;	22 Intermediate 22a) A solution of 1 -(5-chloro-2-hydroxyphenyl)ethanone (3.4 g) in acetone (40 mL) was added potassium carbonate (8.2 g) and the mixture was stirred at ambient temperature for 1 h. Methyl iodide (3.7 g) was added and the reaction mixture was stirred at ambient temperature for 15 h. The suspension was filtered and the volatiles were removed under reduced pressure. The residue was dissolved in Et20 and was washed with water. The organic layer was dried and the volatiles were removed under reduced pressure to yield the desired compound (90% yield).

86%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;	4.1.1.1. 5-Bromo-2-methoxyacetophenone (3a) [46,47]. General procedure: A mixture of 5-Bromo-2-hydroxyacetophenone 2a (10g, 46.5mmol, 1 eq), potassium carbonate (9.62g, 69.75mmol, 1.5 eq) and iodomethane (5.8mL, 93mmol, 2 eq) in DMF (120mL) were stirred overnight in a sealed round bottom flask at room temperature. DMF was removed under reduced pression and the residue was partitioned between water and EtOAc. The combined EtOAc extracts were washed with brine, 0.5M NaOH and then three times with water. The organic layer was dried over MgSO4 and the solvent evaporated. The product was obtained as an off-white solid (9.5g, 89%).
	With potassium carbonate In acetone at 20℃;
	With potassium carbonate In acetone at 20℃;	5 1- (5-chloro-2-methoxyphenyl)ethanone To a suspension of commercially available 5-chloro-2-hydroxyphenyl)ethanone (200mg, 1.17mmol) and powder potassium carbonate (0.5g, 3.9mmol) in acetone (2mL) was added methyl iodide (0.1 OmL, 1.75mmol, 1.5eq) and the mixture was stirred at room temperature for 1 night. Et20 (20mL) was added and the resulting organic phase was washed with HCL IN (15mL), water (15mL) and dried (Na2S04). The solvent was evaporated and the resulting benzonitrile derivative 3 was used directly without further purification. (Yield 79%). NMR (400MHZ, CDC13): 7.66 (1H, d), 7.38 (1H, dd), 6.88 (1H, dd), 3.88 (3H, s), 2.57 (3H, s).
	With potassium carbonate In acetone; benzene	R.6.1 (1) (1) 5-Chloro-2-methoxyacetophenone a-3 To a solution of 30.5 g of 5-chloro-2-hydroxyacetophenone a-2 in 200 ml of acetone were added 26 ml of methyl iodide and 123 g of potassium carbonate, and the mixture was refluxed for 2.5 hr. After cooling, the reaction mixture was filtered, and the solvent was distilled off. Benzene was added to the residue, and the mixture was filtered. Then, the benzene was evaporated leaving 33.0 g of Compound a-3 . m.p.: 31-32 °C

Reference： [1]Current Patent Assignee: NOVO NORDISK A/S - WO2005/19184, 2005, A1 Location in patent: Page/Page column 74
[2]Current Patent Assignee: Gruenenthal Pharma GmbH & Co. Kommanditgesellschaft - US2014/194452, 2014, A1 Location in patent: Paragraph 0434-0436
[3]Current Patent Assignee: Gruenenthal Pharma GmbH & Co. Kommanditgesellschaft - WO2014/108336, 2014, A1 Location in patent: Page/Page column 56
[4]Bouhedja, Mourad; Peres, Basile; Fhayli, Wassim; Ghandour, Zeinab; Boumendjel, Ahcène; Faury, Gilles; Khelili, Smail [European Journal of Medicinal Chemistry, 2018, vol. 144, p. 774 - 796]
[5]Zhong, Zhenlin; Snowden, Timothy S.; Best, Michael D.; Anslyn, Eric V. [Journal of the American Chemical Society, 2004, vol. 126, # 11, p. 3488 - 3495]
[6]Current Patent Assignee: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITY OF MONTPELLIER; UNIVERSITY OF STRASBOURG; NATIONAL INSTITUTE OF HEALTH AND MEDICAL RESEARCH - WO2016/16370, 2016, A1 Location in patent: Page/Page column 44
[7]Current Patent Assignee: SHIONOGI & CO., LTD. - EP227100, 1987, A2

13
[ 1450-74-4 ]
[ 139755-99-0 ]
[ 778639-44-4 ]

Reference： [1]Journal of Heterocyclic Chemistry,2004,vol. 41,p. 541 - 548

14
[ 1450-74-4 ]
[ 139756-00-6 ]
[ 778639-51-3 ]

Yield	Reaction Conditions	Operation in experiment
55%	With trichlorophosphate In pyridine at 0 - 5℃;

Reference： [1]Joshi; Karale; Bhirud; Gill [Journal of Heterocyclic Chemistry, 2004, vol. 41, # 4, p. 541 - 548]

15
[ 1450-74-4 ]
[ 105-58-8 ]
[ 19484-57-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: 5-chloro-2-hydroxyacetophenone With sodium hydride In toluene; mineral oil Stage #2: Diethyl carbonate In toluene; mineral oil Reflux; Stage #3: With hydrogenchloride In water
68%	Stage #1: 5-chloro-2-hydroxyacetophenone With sodium hydride In toluene at 0℃; for 0.333333h; Inert atmosphere; Stage #2: Diethyl carbonate at 110℃; for 4h; Inert atmosphere;
66%	With sodium hydride In toluene at 20 - 100℃;

66%	Stage #1: 5-chloro-2-hydroxyacetophenone; Diethyl carbonate With sodium In toluene at 0 - 130℃; for 4.41667h; Heating / reflux; Stage #2: With hydrogenchloride In water	1 Example 1. 6-chloro-4-hydroxycoumarin (2) [L0094]] To a cooled [(0°C)] suspension of sodium in toluene (7.7 g of the 30% by weight suspension, 100 mmol) in a flame dried flask was added dropwise 2-hydroxy-5-chloroacetophenone [(1. 7] g, 10 mmol) in 40 mL diethylcarbonate over a period of 25 minutes. The reaction mixture was allowed to warm to room temperature and then heated to reflux (about 130 [°C)] for 4 h. The reaction was monitored by LC-MS, the product was detected in negative ion mode. The cooled reaction mixture was quenched with MeOH (15 mL), then poured over ice water (150 mL) and extracted with ether (3 x 50 mL). The aqueous phase was acidified to pH 1.0 by slow dropwise addition of concentrated [HC1] (20 mL) (vigorous gas evolution) until a creamy white precipitate was formed. The precipitate was filtered off and dried affording the title compound 1.3 g, (66 [%)] as an off white solid that was used directly in the next step. [1H] NMR (300 MHz, MeOD-d4) 8 5.651 [(1H,] s), 7.316-7. 346 [(1H,] d, j = 9. 0 Hz), 7.585-7. 623 (1H, dd, [J = 2.] 4,9. 0 Hz), 7.838-7. 847 (1H, d, j = 2. 52 Hz.)
	With sodium hydride In mineral oil at 20 - 100℃; for 2.5h;
	With sodium hydride In toluene at 110℃;
	With sodium hydride In mineral oil at 0℃; for 5h; Reflux;
	Stage #1: 5-chloro-2-hydroxyacetophenone With sodium hydride In toluene for 0.25h; Inert atmosphere; Cooling with ice; Stage #2: Diethyl carbonate In toluene at 20℃; for 5.5h; Inert atmosphere; Reflux;	Preparation of 4-hydroxycoumarin (step 1) General procedure: Preparation of 4-hydroxycoumarin (step 1)9aA solution of 2-hydroxy-5-methoxyacetophenone (9 mmol,1.5 g) in toluene (15 mL) was added dropwise to a dry three-neckround-bottom flask containing sodium hydride (60% w/w suspension,45 mmol, 1.8 g) in toluene (10 mL). This was done under N2atmosphere at ice bath temperature. The mixturewas stirred at thesame temperature for 15 min and followed by the dropwise additionof diethylcarbonate (13.5 mmol, 1.6 g) in toluene (10 mL). Aftercomplete addition, the reaction mixturewas stirred at rt for 30 minand refluxed for five more hours. The reaction mixture wasquenched at ice bath temperature by slow addition of water(20 mL) and acidified with 2 N HCl. The product obtained as a solidprecipitate was filtered, washed with water, and dried under vacuumto get 4-hydroxy-6-methoxy-2H-chromen-2-one as a whitesolid (1.4 g, 82%). This product was directly used in step 2.
	With sodium hydride at 100℃; for 3h;
	With sodium hydride In toluene Inert atmosphere; Reflux;	2 5.1.2. General procedure for the synthesis of 4-hydroxycoumarin intermediates General procedure: Sodium hydride (6 equiv.) was stirred in anhydrous toluene under nitrogen gas. The appropriate 2'-hydroxyacetophenone (1 equiv.) in anhydrous toluene was added dropwise with stirring. After evolution of hydrogen had ceased, diethylcarbonate (2 equiv.) in dry toluene was added dropwise. The reaction mixture was refluxed at 110°C for 6 h then cooled to room temperature. The flask was then put in an ice bath and distilled water (30 mL) added slowly. HCl (2 M) was added dropwise to form a thick precipitate which was filtered under suction to yield the desired 4-hydroxycoumarin intermediates.
	Stage #1: 5-chloro-2-hydroxyacetophenone With sodium hydride In toluene at 0℃; for 0.25h; Inert atmosphere; Stage #2: Diethyl carbonate In toluene Inert atmosphere;	4.2.1. Typical procedure for the synthesis of 1 In a 250 mL two-neck round-bottom flask, 9 mmol of ohydroxyacetophenonein 15 mL toluene was slowly added to sodiumhydride (60% w/w suspension, 5 equiv, 45 mmol, 1.8 g) intoluene (10 mL) under N2 atmosphere at 0 C. After 15 min,13.5 mmol of diethyl carbonate in 10 mL toluene was added dropwise,and the mixture was stirred at room temperature for 30 minand refluxed until the reaction finished (monitored by TLC (ThinLayer Chromatography)). After the mixture cooled to room temperature,the reaction was quenched by slowly addition of 2 N hydrochloricacid. The resulting precipitate was further purified by ashort silica gel column chromatography to give a white solid.
	Stage #1: 5-chloro-2-hydroxyacetophenone With sodium hydride In toluene at 0℃; for 0.25h; Stage #2: Diethyl carbonate In toluene at 0 - 120℃;
	With sodium hydride In toluene
	With sodium hydride at 0 - 110℃; for 4h;
	Stage #1: 5-chloro-2-hydroxyacetophenone With sodium hydride In toluene at 20℃; for 0.5h; Cooling with ice; Stage #2: Diethyl carbonate In toluene for 4h; Reflux;

Reference： [1]Location in patent: experimental part Zhao, Pei-Liang; Wang, Le; Zhu, Xiao-Lei; Huang, Xiaoqin; Zhan, Chang-Guo; Wu, Jia-Wei; Yang, Guang-Fu [Journal of the American Chemical Society, 2010, vol. 132, # 1, p. 185 - 194]
[2]Kumari, Priti; Gupta, Sonal; Narayana, Chintam; Ahmad, Shakeel; Vishnoi, Nidhi; Singh, Shailja; Sagar, Ram [New Journal of Chemistry, 2018, vol. 42, # 16, p. 13985 - 13997]
[3]Kym, Philip R.; Iyengar, Rajesh; Souers, Andrew J.; Lynch, John K.; Judd, Andrew S.; Gao, Ju; Freeman, Jennifer; Mulhern, Mathew; Zhao, Gang; Vasudevan, Anil; Wodka, Dariusz; Blackburn, Christopher; Brown, Jim; Che, Jennifer Lee; Cullis, Courtney; Lai, Su Jen; LaMarche, Matthew J.; Marsilje, Tom; Roses, Jon; Sells, Todd; Geddes, Brad; Govek, Elizabeth; Patane, Michael; Fry, Dennis; Dayton, Brian D.; Brodjian, Sevan; Falls, Doug; Brune, Michael; Bush, Eugene; Shapiro, Robin; Knourek-Segel, Victoria; Fey, Thomas; McDowell, Cathleen; Reinhart, Glenn A.; Preusser, Lee C.; Marsh, Kennan; Hernandez, Lisa; Sham, Hing L.; Collins, Christine A. [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5888 - 5891]
[4]Current Patent Assignee: ABBVIE INC - WO2003/106452, 2003, A2 Location in patent: Page 77-78
[5]Location in patent: scheme or table Nolan, Karen A.; Doncaster, Jeremy R.; Dunstan, Mark S.; Scott, Katherine A.; Frenkel, A. David; Siegel, David; Ross, David; Barnes, John; Levy, Colin; Leys, David; Whitehead, Roger C.; Stratford, Ian J.; Bryce, Richard A. [Journal of Medicinal Chemistry, 2009, vol. 52, # 22, p. 7142 - 7156]
[6]Peng, Shiyong; Wang, Lei; Huang, Jiayao; Sun, Shaofa; Guo, Haibing; Wang, Jian [Advanced Synthesis and Catalysis, 2013, vol. 355, # 13, p. 2550 - 2557] Peng, Shiyong; Gao, Tao; Sun, Shaofa; Peng, Yanhong; Wu, Minghu; Guo, Haibing; Wang, Jian [Advanced Synthesis and Catalysis, 2014, vol. 356, # 2-3, p. 319 - 324]
[7]Hack, Daniel; Chauhan, Pankaj; Deckers, Kristina; Hermann, Gary N.; Mertens, Lucas; Raabe, Gerhard; Enders, Dieter [Organic Letters, 2014, vol. 16, # 19, p. 5188 - 5191]
[8]Rao, Maddali L.N.; Kumar, Abhijeet [Tetrahedron, 2014, vol. 70, # 39, p. 6995 - 7005]
[9]Jayaprakash, Rao Y.; Chakravarthula, Venu [Journal of Heterocyclic Chemistry, 2015, vol. 52, # 4, p. 1014 - 1018]
[10]Mutai, Peggoty; Breuzard, Gilles; Pagano, Alessandra; Allegro, Diane; Peyrot, Vincent; Chibale, Kelly [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 5, p. 1652 - 1665]
[11]Chu, Xianglong; Tang, Ziqiang; Ma, Jiangshan; He, Libowen; Feng, Lei; Ma, Chen [Tetrahedron, 2018, vol. 74, # 9, p. 970 - 974]
[12]Kumar, K. Shiva; Ramulu, Meesa Siddi; Kumar, N. Praveen [New Journal of Chemistry, 2018, vol. 42, # 14, p. 11276 - 11279]
[13]Hoppe, Heinrich C.; Isaacs, Michelle; Kaye, Perry T.; Krause, Rui W. M.; Manyeruke, Meloddy H.; Seldon, Ronnett; Tshiwawa, Thendamudzimu; Warner, Digby F. [Bioorganic and medicinal chemistry letters, 2020]
[14]Bhimapaka, China Raju; Karri, Shailaja; Kuncha, Madhusudana; Kurma, Siva Hariprasad; Sistla, Ramakrishna [Bioorganic and medicinal chemistry letters, 2020, vol. 30, # 16]
[15]Feng, Xi; Qin, Zhen; Cheng, Xinying; Liu, Dongyu; Peng, Yinghe; Huang, Huidan; Song, Bin; Bian, Jinlei; Li, Zhiyu [Journal of Organic Chemistry, 2021, vol. 86, # 18, p. 12537 - 12548]

16
[ 1450-74-4 ]
[ 70-11-1 ]
[ 303145-32-6 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 1h; Inert atmosphere;
68%	With potassium carbonate In acetonitrile for 4h; Heating;

Reference： [1]Dias, Herbert J.; Vieira, Tatiana M.; Crevelin, Eduardo J.; Donate, Paulo M.; Vessecchi, Ricardo; Crotti, Antônio E.M. [Journal of Mass Spectrometry, 2017, vol. 52, # 12, p. 809 - 816]
[2]Gündoǧdu-Karaburun, Nalan; Benkli, Kadriye; Tunali, Yaǧmur; Uçucu, Ümit; Demirayak, Şeref [European Journal of Medicinal Chemistry, 2006, vol. 41, # 5, p. 651 - 656]

17
[ 1450-74-4 ]
[ 536-38-9 ]
[ 131866-23-4 ]

Yield	Reaction Conditions	Operation in experiment
73%	With tetra-(n-butyl)ammonium iodide; sodium carbonate In water for 0.5h; Reflux; Green chemistry;	Synthesis of 2-aroylbenzofurans General procedure: Synthesis of 2-(4-bromobenzoyl)-3-methylbenzofuran 3a A mixture of o-hydroxyacetophenone (1.36 g, 0.01 mol), α-bromoketone (2.62 g, 0.01 mol), Na2CO3 (2.12 g, 0.02 mol) and n-Bu4N+I- (0.01 mol) was mixed in a mortar with pestle. This mixture was transferred to a round-bottom flask containing 10.0 ml water and then refluxed on a heating mantle. After completion of the reaction (30 min, TLC), the reaction mixture was cooled at room temperature. The brown-colored solid thus obtained was filtered, dried, and purified by column chromatography on silica gel (100-200 mesh) using petroleum ether/ethyl acetate as eluent mixture (petroleum ether:EtOAc::99:1) to remove the coloured impurities that furnished the pure white product. The other 2-aroylbenzofurans 3b-e and 3a'-e' were also synthesized following a similar procedure by condensing the respective o-hydroxyacetophenones with α-bromoketones.
65%	With potassium carbonate In acetonitrile for 4h; Heating;

Reference： [1]Jindal, Pooja; Sharma, Geeta; Arora, Rita; Kamboj, Ramesh C. [Research on Chemical Intermediates, 2015, vol. 41, # 7, p. 4465 - 4476]
[2]Gündoǧdu-Karaburun, Nalan; Benkli, Kadriye; Tunali, Yaǧmur; Uçucu, Ümit; Demirayak, Şeref [European Journal of Medicinal Chemistry, 2006, vol. 41, # 5, p. 651 - 656]

18
[ 1450-74-4 ]
[ 86176-56-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 2 h / 80 - 90 °C 2: 70 percent / NH₂OH*HCl / ethanol / 0.5 h / Heating
	Multi-step reaction with 2 steps 1: 2 h / 90 - 100 °C 2: hydroxylamine hydrochloride / ethanol / 0.5 h / Reflux

Reference： [1]Ghosh, Tarun; Saha, Satyajit; Bandyopadhyay, Chandrakanta [Synthesis, 2005, # 11, p. 1845 - 1849]
[2]Tong, Pei; Sun, Zhou; Wang, Shutao; Zhang, Yuan; Li, Ying [Journal of Organic Chemistry, 2019, vol. 84, # 21, p. 13967 - 13974]

19
[ 1450-74-4 ]
[ 133406-29-8 ]

Reference： [1]Russian Chemical Bulletin,2000,vol. 49,p. 478 - 481

20
[ 1450-74-4 ]
[ 37674-72-9 ]

Reference： [1]Synthesis,1989,p. 709 - 710

21
[ 1450-74-4 ]
[ 42926-52-3 ]
[ 857842-86-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 55℃;	Example 32b: 5-Chloro-2- (2-ethoxvbenzovloxy)-acetophenone; To a solution of 5-chloro-2-hydroxyacetophenone (1.47 g, 8.66 mmol) in triethylamine (2.18 g, 21.66 mmol) and dry THF (30 ml) is added <strong>[42926-52-3]2-ethoxybenzoyl chloride</strong> (1. 6 g, 8.66 mmol). The mixture is heated at 55tC overnight. The volatiles are removed at reduced pressure and the resulting residue is diluted with ethyl acetate and washed with brine. Drying of the resulting solution over sodium sulfate, evaporation of the solvent and chromatography on silicagel yields the title compound.'H-NMR (CDCI3, 400 MHz): 8.03 (d, 1 H) ; 7.79 (s, 1 H) ; 7.53-7. 49 (m, 2H); 7.18 (d, 1 H) ; 7.03-7. 00 (m, 2H); 4.13 (q, 2H); 2.62 (s, 3H); 1.44 (s, 3H).

Reference： [1]Patent: WO2005/61476,2005,A2 .Location in patent: Page/Page column 86

22
[ 1450-74-4 ]
[ 6342-64-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium carbonate; methyl iodide In acetonitrile at 85℃; for 18h;	16 Dissolve 5'-chloro-2'-hydroxyacetophenone (15.3594 g, 90.03 mmol) in 100 mL of anhydrous acetonitrile in a pressure vessel. Add K2CO3 (13.7541 g, 99.52 mmol) and MeI (25.56 ML, 180.06 mmol) to the vessel. Seal the vessel and heat the reaction mixture TO 85°C FOR 18 HOURS. Cool the reaction and concentrate it in vacuo. Partition the residue between ET20 and H20. WASH the organic layers with 2N NAOH (2X). Dry the combined organic layers with MGS04. Filter off the drying agent and concentrate in vacuo to afford 13.15 g of 1- (5-CHLORO-2-METHOXY-PHENYL)-ETHANONE (79%). Suspend CuBr2 (29.44 g, 131.81 mmol) in 150 mL EtOAc and heat it to reflux. Dissolve 1- (5-CHLORO-2-METHOXY-PHENYL)-ETHANONE (13.15 g, 71.23 mmol) in 100 mL of CHC13 and add it dropwise to the reaction. After 4 hours, filter the reaction to remove the solids. Concentrate the filtrate in vacuo and dissolve the residue in EtOAc. Wash the organic layer with saturated aqueous NAHCO3 and water. Dry the organic layer with MGS04. Filter off the drying agent and concentrate in vacuo to afford 17.07 g of 2- BROMO-1- (5-CHLORO-2-METHOXY-PHENYL)-ETHANONE. Dissolve 2-BROMO-L- (5-CHLORO-2-METHOXY-PHENYL)-ETHANONE (17.07 g, 64.78 mmol) in 150 mL of CHC13 and add hexamethylenetetramine (9.09 g, 64.84 mmol) to the reaction mixture. Allow the reaction to stir at ambient temperature for 23 hours. Collect the solids via filtration and wash the solids with ET20. Slurry the solid in 100 mL of MEOH and add 50 ML of concentrated HCl to it dropwise. Heat the reaction to reflux and allow it to stir for 23 hours. Cool the reaction to ambient temperature and filter off the solids. Slurry the filtrate in MEOH and again collect the solids via filtration. Concentrate the filtrate to afford 10.99 g of 2-amino-1- (5-chloro-2-methoxy-phenyl)-ethanone hydrochloride. Dissolve 1- [3- (DIMETHYLAMINO) propyl] -3-ethylcarbodiimide hydrochloride (8.0362 g, 41.92 mmol), 4- (dimethylamino) pryidine (1.0525g, 8. 62 mmol) and adipic acid monomethyl ester (6.71 g, 41.90 mmol) in 100 mL of CH2C12 and allow it to stir at room temperature for 45 minutes. Add crude 2-amino-l- (5-chloro-2-methoxy-phenyl)- ethanone hydrochloride (10.99 g, 46.55 mmol) and triethylamine (9.42 g, 93.1 mmol) to the reaction mixture and allow it to stir at ambient temperature for 21 hours. Dilute the reaction with 200 mL of CH2CI2 and wash it with 1 N HC1 (2X), saturated aqueous NAHCO3 (2X) and brine (1X). Dry the organic layer with MGS04. Filter off the drying agent and concentrate in vacuo to afford 9.39 g of the crude titled product: mass spectrum: m/z = 342.1 (M+H).

Reference： [1]Current Patent Assignee: NOVO NORDISK A/S - WO2005/19184, 2005, A1 Location in patent: Page/Page column 43-44

23
[ 1450-74-4 ]
[ 82386-89-8 ]
[ 105-56-6 ]
[ 931112-50-4 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 67 A solution of 5-chloro-2-hydroxyacetophenone (25 g), 2-chloro-5-trifluoromethylbenzaldehyde (30.5 g), ethyl cyanoacetate (15.5 mL) and ammonium acetate (56 g) in ethanol (500 mL) was refluxed for 3 hours, cooled, poured into water and ethyl acetate and stirred for 24 hours. The extract was washed with brine, concentrated to 250 mL and filtered. 1H NMR (300 MHz, DMSO-d6) delta 8.00 (brs, 1H), 7.94 (s, 1H), 7.93 (s, 1H), 7.68 (m, 2H), 7.40 (dd, 1H), 6.99 (d, 1H).

Reference： [1]Patent: US2007/72833,2007,A1 .Location in patent: Page/Page column 25

24
[ 1450-74-4 ]
[ 82386-89-8 ]
C₁₆H₉Cl₂F₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 62A A solution of 5-chloro-2-hydroxyacetophenone (4.6 g), 2-chloro-5-trifluoromethylbenzaldehyde (3.92 mL) and NaOH (1.3 g) in diethyl ether (50 mL) and water (25 mL) was stirred for 72 hours, poured into 1M HCl (100 mL) and extracted with diethyl ether. The extract was washed with brine, concentrated and recrystallized from diethyl ether/hexane.

Reference： [1]Patent: US2007/72833,2007,A1 .Location in patent: Page/Page column 25

25
[ 110-86-1 ]
[ 1450-74-4 ]
[ 4146-43-4 ]
[ 6046-93-1 ]
(Cu(NC₅H₅)OC₆H₃ClC(CH₃)NNCO)2(CH₂)2 [ No CAS ]

Reference： [1]Russian Chemical Bulletin,2003,vol. 52,p. 1301 - 1304

26
[ 32161-06-1 ]
[ 1450-74-4 ]
[ 1069133-33-0 ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 6407 - 6410

27
[ 1450-74-4 ]
[ 459-57-4 ]
[ 908563-71-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium hydroxide In ethanol; water at 20℃;	Route A General procedure: To a solution of the selected acetophenone (1.0 eq) and aldehyde (1.1 eq) in EtOH (10 mL)a KOH aqueous solution (50% p/v, 1 mL) was added dropwise and reaction mixture was stirredovernight at rt, diluted with H2O, and neutralized with aqueous 6N HCl. The formed solid/semisolid product was collected by vacuum filtration or extracted with a suitable solvent. The crude of reactionwas then purified by column chromatography or by crystallization.
63%	With potassium hydroxide In ethanol at 20℃;
	With sodium hydroxide In ethanol; water at 20℃;

	With potassium hydroxide In ethanol
	With potassium hydroxide In ethanol at 0 - 20℃;	General procedure for the synthesis of compounds 2a-f General procedure: 2-Hydoxyacetophenones 1a-f (0.01 mol) and 4-fluorobenzaldehyde (0.01 mol) were added to a solution of KOH (0.03 mol) in ethanol (15 mL) at 0-5 °C. The reaction mixture was stirred 2-3 h at room temperature. Then the reaction mixture was poured over crushed ice and neutralized carefully with 2 N HCl, and the obtained precipitate was filtered, washed with water, and dried. The crude product was crystallized with chloroform-ethanol to afford desired compound.
	With potassium hydroxide In ethanol at 20℃;

Reference： [1]Bonvicini, Francesca; Gentilomi, Giovanna A.; Bressan, Francesca; Gobbi, Silvia; Rampa, Angela; Bisi, Alessandra; Belluti, Federica [Molecules, 2019, vol. 24, # 2]
[2]Location in patent: experimental part Ghotekar; Mandhane; Joshi; Bhagat; Gill [Indian Journal of Heterocyclic Chemistry, 2010, vol. 19, # 4, p. 341 - 344]
[3]Location in patent: experimental part Lorenz, Michael; Shahjahan Kabir; Cook, James M. [Tetrahedron Letters, 2010, vol. 51, # 7, p. 1095 - 1098]
[4]Location in patent: scheme or table Ghotekarab; Joshia; Mandhane; Bhagata; Gill [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 9, p. 1267 - 1270]
[5]Dofe, Vidya S.; Sarkate, Aniket P.; Lokwani, Deepak K.; Kathwate, Santosh H.; Gill, Charansingh H. [Research on Chemical Intermediates, 2017, vol. 43, # 1, p. 15 - 28]
[6]Dofe, Vidya S.; Sarkate, Aniket P.; Shaikh, Zarina M.; Gill, Charansingh H. [Heterocyclic Communications, 2018, vol. 24, # 1, p. 59 - 65]

28
[ 1450-74-4 ]
[ 677304-69-7 ]
[ 79099-07-3 ]
[ 1031413-71-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2383 - 2388

29
[ 1450-74-4 ]
[ 1134-00-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 0.5 h / Inert atmosphere 1.2: Inert atmosphere; Reflux 2.1: sodium hydroxide / tetrahydrofuran / 20 °C
	Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: lithium hydroxide / methanol; water
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.42 h / 20 °C 1.2: 12 h / 20 °C 2.1: sodium ethanolate; ethanol / 12 h / Reflux

Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 6 h / Reflux 2: sodium ethanolate / toluene; ethanol / 12 h / Inert atmosphere; Reflux

Reference： [1]Piemontese, Luca; Carbonara, Giuseppe; Fracchiolla, Giuseppe; Laghezza, Antonio; Tortorella, Paolo; Loiodice, Fulvio [Heterocycles, 2010, vol. 81, # 12, p. 2865 - 2872]
[2]Friberg, Anders; Vigil, Dominico; Zhao, Bin; Daniels, R. Nathan; Burke, Jason P.; Garcia-Barrantes, Pedro M.; Camper, Demarco; Chauder, Brian A.; Lee, Taekyu; Olejniczak, Edward T.; Fesik, Stephen W. [Journal of Medicinal Chemistry, 2013, vol. 56, # 1, p. 15 - 30]
[3]Current Patent Assignee: VANDERBILT UNIVERSITY - WO2014/47427, 2014, A2
[4]Youssif, Bahaa G.M.; Mohamed, Ashraf M.; Osman, Essam Eldin A.; Abou-Ghadir, Ola F.; Elnaggar, Dina H.; Abdelrahman, Mostafa H.; Treamblu, Laurent; Gomaa, Hesham A.M. [European Journal of Medicinal Chemistry, 2019, vol. 177, p. 1 - 11]

30
[ 1450-74-4 ]
[ 1458-98-6 ]
[ 1210038-71-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 4h;	2 5'-Chloro-2'-(2-methyl-2-propenyloxy)acetophenone (Reference compound No.2-1) Reference Example 2 5'-Chloro-2'-(2-methyl-2-propenyloxy)acetophenone (Reference compound No.2-1) A suspension of 5'-chloro-2'-hydroxyacetophenone (0.86 g, 5.0 mmol), potassium carbonate (1.4 g, 10 mmol) and 3-bromo-2-methylpropene (0.56 mL, 5.5 mmol) in anhydrous N,N-dimethylformamide (20 mL) was stirred at 60°C for 4 hours. After cooling, the reaction mixture was diluted with water (100 mL), and the whole was extracted with ethyl acetate (100 mL). The organic layer was washed with saturated aqueous ammonium chloride solution (50 mL) and brine (50 mL) and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to give the title reference compound (1.1 g) as orange oil (Yield 96%). 5'-Chloro-2'-(2-methyl-2-propenyloxy)acetophenone (Reference compound No.2-1) 1H-NMR (500 MHz, CDCl3) δ 1.85 (s, 3H), 2.63 (s, 3H), 4.52 (s, 2H), 5.05 (t, J = 1.1 Hz, 1H), 5.10 (t, J = 1.1 Hz, 1H), 6.89 (d, J = 8.9 Hz, 1H), 7.37 (dd, J = 8.9, 2.7 Hz, 1H), 7.70 (d, J = 2.7 Hz, 1H);
	With potassium carbonate	22.1 1-(5-chloro-2-((2-methylallyl)oxy)phenyl)ethan-1-one Step 1 1-(5-chloro-2-((2-methylallyl)oxy)phenyl)ethan-1-one 1-(5-chloro-2-hydroxyphenyl)ethan-1-one 22a (5.1 g, 30 mmol) was dissolved in 50 ml of N,N-dimethylformamide, then added with 3-bromo-2-methylpropene (4.86 g, 36 mmol) and potassium carbonate (8.29 g, 60 mmol) sequentially, and reacted at room temperature overnight. After the reaction was completed, the reaction solution was added with 100 mL of water and extracted with ethyl acetate (50 mL3), organic phases were combined, washed with saturated brine (50 mL2), dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain 1-(5-chloro-2-((2-methylallyl)oxy)phenyl)ethan-1-one 22b (6.72 g, yellow oily substance), and the product was directly used for the next reaction without further purification. MS m/z(ESI): 225.0 [M+1]
6.72 g	With potassium carbonate In N,N-dimethyl-formamide at 20℃;	22.1 1-(5-chloro-2-((2-methylallyl)oxy)phenyl)ethan-1-one 1-(5-chloro-2-hydroxyphenyl)ethan-1-one 22a (5.1 g, 30 mmol) was dissolved in 50 ml of N,N-dimethylformamide, then added with 3-bromo-2-methylpropene (4.86 g, 36 mmol) and potassium carbonate (8.29 g, 60 mmol) sequentially, and reacted at room temperature overnight. After the reaction was completed, the reaction solution was added with 100 mL of water and extracted with ethyl acetate (50 mL×3), organic phases were combined, washed with saturated brine (50 mL×2), dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain 1-(5-chloro-2-((2-methylallyl)oxy)phenyl)ethan-1-one 22b (6.72 g, yellow oily substance), and the product was directly used for the next reaction without further purification. MS m/z(ESI): 225.0 [M+1]

Reference： [1]Current Patent Assignee: SANTEN PHARMACEUTICAL CO LTD - EP2319831, 2011, A1 Location in patent: Page/Page column 13
[2]Current Patent Assignee: HISUN GROUP CO., LTD.; HISUN ACCURAY THERAPEUTICS; SHANGHAI ANGRUI PHARMACEUTICAL TECH - EP3974434, 2022, A1
[3]Current Patent Assignee: HISUN GROUP CO., LTD.; HISUN ACCURAY THERAPEUTICS; SHANGHAI ANGRUI PHARMACEUTICAL TECH - EP3974434, 2022, A1 Location in patent: Paragraph 0259-0260

31
[ 1450-74-4 ]
[ 73220-38-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 2 h / 100 °C 2: bromine / chloroform / 0.08 h / 0 - 23 °C

Reference： [1]Bryan, Marian C.; Biswas, Kaustav; Peterkin, Tanya A.N.; Rzasa, Robert M.; Arik, Leyla; Lehto, Sonya G.; Sun, Hong; Hsieh, Feng-Yin; Xu, Cen; Fremeau, Robert T.; Allen, Jennifer R. [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 619 - 622]

32
[ 6342-64-9 ]
[ 1450-74-4 ]

Yield	Reaction Conditions	Operation in experiment
	With boron tribromide In dichloromethane at -78 - 23℃; for 1h;

Reference： [1]Location in patent: scheme or table Bryan, Marian C.; Biswas, Kaustav; Peterkin, Tanya A.N.; Rzasa, Robert M.; Arik, Leyla; Lehto, Sonya G.; Sun, Hong; Hsieh, Feng-Yin; Xu, Cen; Fremeau, Robert T.; Allen, Jennifer R. [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 619 - 622]

33
[ 55877-79-7 ]
[ 1450-74-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 619 - 622

34
[ 1450-74-4 ]
[ 1208-88-4 ]
[ 1355360-74-5 ]

Reference： [1]Bulletin of the Korean Chemical Society,2011,vol. 32,p. 3887 - 3892
[2]Phosphorus, Sulfur and Silicon and the Related Elements,2012,vol. 187,p. 327 - 335

35
[ 1450-74-4 ]
[ 1208-88-4 ]
[ 1355360-81-4 ]

Reference： [1]Bulletin of the Korean Chemical Society,2011,vol. 32,p. 3887 - 3892

36
[ 1450-74-4 ]
[ 923224-97-9 ]
[ 1423715-32-5 ]

Yield	Reaction Conditions	Operation in experiment
31.3%	With acetic acid In methanol at 120℃; for 0.5h; Microwave irradiation;	52 PREPARATION OF (E)-N'-(1 -(5-CHLORO-2-HYDROXYPHENYL)ETHYLIDENE)-3- (1 ,1 -DIOXIDOTHIOMORPHOLINO)BENZOHYDRAZIDE. 3-(1 ,1-dioxidothiomorpholino)benzohydrazide (30 mg, 0.111 mmol) and 1-(5-chloro-2-hydroxyphenyl)ethanone (19.00 mg, 0.1 11 mmol) was dissolved in methanol (Volume: 4 ml) in the presence of acetic acid as a catalyst and then the reaction mixture was heated via microwave irradiation to 120 °C for 30 min. Reaction was monitored by TLC. After completion of the reaction, following cooling, the solvent was removed by vacuum and the resulting crude material was purified by flash column chromatography (2% CH3OH/CH2CI2) afforded the title compound (E)- N'-(1-(5-chloro-2-hydroxyphenyl)ethylidene)-3-(1 ,1- dioxidothiomorpholino)benzohydrazide (15 mg, 0.035 mmol, 31.3 % yield) as a solid. 1 H NMR (DMSO-d6, 400 MHz): δ 7.65 (d, 1 H, J = 2.0 Hz), 7.47 (m, 1 H), 7.41 (t, 1 H, J = 7.6 Hz), 7.36-7.27 (m, 3H), 6.94 (d, 1 H, J = 8.8 Hz), 3.87 (m, 4H), 3.17 (m, 4H), 2.48 (s, 3H). Mass [M+H]+ :422.2

Reference： [1]Current Patent Assignee: UNIVERSITY OF UTAH - WO2013/25805, 2013, A1 Location in patent: Paragraph 00267

37
[ 1450-74-4 ]
[ 1423715-36-9 ]
[ 1423715-37-0 ]

Yield	Reaction Conditions	Operation in experiment
53.4%	With acetic acid In methanol at 120℃; for 0.5h; Microwave irradiation;	63 PREPARATION OF (E)-N'-(1 -(5-CHLORO-2-HYDROXYPHENYL)ETHYLIDENE)-3-((4- ETHYLPIPERAZIN-1 -YL)SULF0NYL) BENZOHYDRAZIDE. 3-((4-methylpiperazin-1-yl)sulfonyl)benzohydrazide (85 mg, 0.285 mmol) and 1-(5-chloro-2-hydroxyphenyl)ethanone (48.6 mg, 0.285 mmol) was dissolved in methanol (Volume: 4 ml) in the presence of acetic acid as a catalyst and then the reaction mixture was heated via microwave irradiation to 120 °C for 30 min. Reaction was monitored by TLC. After completion of the reaction, following cooling, the solvent was removed by vacuum and the resulting crude material was purified by flash column chromatography (2% CH3OH/CH2CI2) afforded the product (E)-N'-(1-(5- chloro-2-hydroxyphenyl)ethylidene)-3-((4-methylpiperazin-1- yl)sulfonyl)benzohydrazide (70 mg, 0.152 mmol, 53.4 % yield) as a solid. 1 H NMR (CD30D, 400 MHz): δ 8.29 (s, 1 H), 8.21 (d, 1 H, J = 7.2 Hz), 7.99 (d, 1 H, J = 8.0 Hz), 7.78 (t, 1 H, J = 7.6 Hz), 7.59 (d, 1 H, J = 2.4 Hz), 7.27 (dd, 1 H, J = 2.4 & 9.2 Hz), 6.92 (d, 1 H, J = 8.8 Hz), 3.09 (m, 4H), 2.54 (m, 4H), 2.48 (s, 3H), 2.28 (s, 3H). Mass [M+H]+ :450.9

Reference： [1]Current Patent Assignee: UNIVERSITY OF UTAH - WO2013/25805, 2013, A1 Location in patent: Paragraph 00278

38
[ 1450-74-4 ]
[ 1228571-53-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: ammonia / Isopropyl acetate; methanol / 18 h / 5 - 20 °C / Inert atmosphere 2.1: titanium(IV) isopropylate / tetrahydrofuran / 0.5 h / 15 °C / Inert atmosphere 2.2: 0.83 h / Inert atmosphere 3.1: D-tartaric acid / tetrahydrofuran; water / 20 - 50 °C / Inert atmosphere

Reference： [1]Han, Zhengxu S.; Herbage, Melissa A.; Mangunuru, Hari P. R.; Xu, Yibo; Zhang, Li; Reeves, Jonathan T.; Sieber, Joshua D.; Li, Zhibin; Decroos, Philomen; Zhang, Yongda; Li, Guisheng; Li, Ning; Ma, Shengli; Grinberg, Nelu; Wang, Xiaojun; Goyal, Navneet; Krishnamurthy, Dhileep; Lu, Bruce; Song, Jinhua J.; Wang, Guijun; Senanayake, Chris H. [Angewandte Chemie - International Edition, 2013, vol. 52, # 26, p. 6713 - 6717][Angew. Chem., 2013, vol. 125, # 26, p. 6845 - 6849,5]

39
[ 1450-74-4 ]
[ 1228569-39-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: ammonia / Isopropyl acetate; methanol / 18 h / 5 - 20 °C / Inert atmosphere 2.1: titanium(IV) isopropylate / tetrahydrofuran / 0.5 h / 15 °C / Inert atmosphere 2.2: 0.83 h / Inert atmosphere 3.1: L-Tartaric acid / tetrahydrofuran; water / 8 h / 20 - 50 °C / Inert atmosphere

Reference： [1]Han, Zhengxu S.; Herbage, Melissa A.; Mangunuru, Hari P. R.; Xu, Yibo; Zhang, Li; Reeves, Jonathan T.; Sieber, Joshua D.; Li, Zhibin; Decroos, Philomen; Zhang, Yongda; Li, Guisheng; Li, Ning; Ma, Shengli; Grinberg, Nelu; Wang, Xiaojun; Goyal, Navneet; Krishnamurthy, Dhileep; Lu, Bruce; Song, Jinhua J.; Wang, Guijun; Senanayake, Chris H. [Angewandte Chemie - International Edition, 2013, vol. 52, # 26, p. 6713 - 6717][Angew. Chem., 2013, vol. 125, # 26, p. 6845 - 6849,5]

40
[ 1450-74-4 ]
[ 106-42-3 ]
[ 88952-03-8 ]

Yield	Reaction Conditions	Operation in experiment
30%	With tert.-butylhydroperoxide; copper(II) acetate dihydrate In decane at 120℃; for 5.5h; chemoselective reaction;

Reference： [1]Rout, Saroj Kumar; Guin, Srimanta; Banerjee, Arghya; Khatun, Nilufa; Gogoi, Anupal; Patel, Bhisma K. [Organic Letters, 2013, vol. 15, # 16, p. 4106 - 4109]

41
[ 1450-74-4 ]
[ 14615-72-6 ]
[ 105-56-6 ]
[ 1453835-43-2 ]

Yield	Reaction Conditions	Operation in experiment
32%	With ammonium acetate; In ethanol;Reflux;	General procedure: The appropriate acetophenone (2.92 mmol) was dissolved in ethanol (15 ml), followed by addition of appropriate benzaldehyde (2.92 mmol), ethyl cyanoacetate (2.92 mmol) and ammonium acetate (23.39 mmol) and was refluxed overnight. The solvent was reduced; the residue was diluted with ethyl acetate, and washed with water and brine. The combined organic layer was dried over sodium sulfate and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography and recrystallized using ethanol.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 5429 - 5433

42
[ 1450-74-4 ]
[ 1136-45-4 ]
2-acetyl-4-chlorophenyl-5-methyl-3-phenylisoxazole-4-carboxylate [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2013,vol. 50,p. 999 - 1004

43
[ 1450-74-4 ]
[ 4460-86-0 ]
[ 1430207-38-7 ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium hydroxide In ethanol; water at 20℃;	General procedure for synthesis of chalcones via Claisen-Schmidt condensation General procedure: To a solution of 2,4,5-trimethoxy benzaldehyde (4mmol) and appropriate acetophenone (4mmol) in C2H5OH (25ml), 40% of aqueous KOH (2mmol) was added. The reaction mixture was stirred at r.t. till completion of reaction (monitored by TLC). Then the reaction mass was poured into ice water and neutralized with aqueous 10% HCl solution. The precipitate was filtered, washed with excess of water, dried and recrystallized from methanol to obtain pure chalcones.

Reference： [1]Shenvi, Suvarna; Kumar, Krishna; Hatti, Kaushik S.; Rijesh; Diwakar, Latha; Reddy, G. Chandrasekara [European Journal of Medicinal Chemistry, 2013, vol. 62, p. 435 - 442]

44
[ 118-93-4 ]
[ 1450-74-4 ]
[ 3321-92-4 ]
[ 3226-34-4 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 809 - 813

45
[ 3752-25-8 ]
[ 1450-74-4 ]
C₁₇H₁₂Cl₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; trichlorophosphate; at 20℃;Cooling with ice;	General procedure: Phosphoryl chloride (POCl3; 20 mmol) was added slowly to a 100 mL SNRB flask containing a mixture of I (5.5 mmol) and the appropriate 2'-hydroxyacetophenone (5 mmol) in pyridine (30 mL). The flask was placed in an ice bath and the reaction mixture was left overnight, with constant stirring at room temperature. The reaction mixture was then poured into 100 mL cold, dilute HCl in a 250 mL EF, followed by extraction with ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The crude product obtained was further purified by open column chromatography.

Reference： [1]Molecules,2014,vol. 19,p. 16058 - 16081

46
[ 1450-74-4 ]
[ 6099-03-2 ]
C₁₈H₁₅ClO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; trichlorophosphate; at 20℃;Cooling with ice;	General procedure: Phosphoryl chloride (POCl3; 20 mmol) was added slowly to a 100 mL SNRB flask containing a mixture of I (5.5 mmol) and the appropriate 2'-hydroxyacetophenone (5 mmol) in pyridine (30 mL). The flask was placed in an ice bath and the reaction mixture was left overnight, with constant stirring at room temperature. The reaction mixture was then poured into 100 mL cold, dilute HCl in a 250 mL EF, followed by extraction with ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The crude product obtained was further purified by open column chromatography.

Reference： [1]Molecules,2014,vol. 19,p. 16058 - 16081

47
[ 1450-74-4 ]
[ 2316-26-9 ]
C₁₉H₁₇ClO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; trichlorophosphate; at 20℃;Cooling with ice;	General procedure: Phosphoryl chloride (POCl3; 20 mmol) was added slowly to a 100 mL SNRB flask containing a mixture of I (5.5 mmol) and the appropriate 2'-hydroxyacetophenone (5 mmol) in pyridine (30 mL). The flask was placed in an ice bath and the reaction mixture was left overnight, with constant stirring at room temperature. The reaction mixture was then poured into 100 mL cold, dilute HCl in a 250 mL EF, followed by extraction with ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The crude product obtained was further purified by open column chromatography.

Reference： [1]Molecules,2014,vol. 19,p. 16058 - 16081

48
[ 1450-74-4 ]
[ 6972-61-8 ]
C₁₉H₁₇ClO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; trichlorophosphate at 20℃; Cooling with ice;	3.3. General Procedure for the Synthesis of II General procedure: Phosphoryl chloride (POCl3; 20 mmol) was added slowly to a 100 mL SNRB flask containing a mixture of I (5.5 mmol) and the appropriate 2'-hydroxyacetophenone (5 mmol) in pyridine (30 mL). The flask was placed in an ice bath and the reaction mixture was left overnight, with constant stirring at room temperature. The reaction mixture was then poured into 100 mL cold, dilute HCl in a 250 mL EF, followed by extraction with ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The crude product obtained was further purified by open column chromatography.

Reference： [1]Leong, Sze Wei; Mohd Faudzi, Siti Munirah; Abas, Faridah; Mohd Aluwi, Mohd Fadhlizil Fasihi; Rullah, Kamal; Wai, Lam Kok; Abdul Bahari, Mohd Nazri; Ahmad, Syahida; Tham, Chau Ling; Shaari, Khozirah; Lajis, Nordin H. [Molecules, 2014, vol. 19, # 10, p. 16058 - 16081]

49
[ 1450-74-4 ]
[ 10538-51-9 ]
C₁₉H₁₇ClO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; trichlorophosphate at 20℃; Cooling with ice;	3.3. General Procedure for the Synthesis of II General procedure: Phosphoryl chloride (POCl3; 20 mmol) was added slowly to a 100 mL SNRB flask containing a mixture of I (5.5 mmol) and the appropriate 2'-hydroxyacetophenone (5 mmol) in pyridine (30 mL). The flask was placed in an ice bath and the reaction mixture was left overnight, with constant stirring at room temperature. The reaction mixture was then poured into 100 mL cold, dilute HCl in a 250 mL EF, followed by extraction with ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The crude product obtained was further purified by open column chromatography.

Reference： [1]Leong, Sze Wei; Mohd Faudzi, Siti Munirah; Abas, Faridah; Mohd Aluwi, Mohd Fadhlizil Fasihi; Rullah, Kamal; Wai, Lam Kok; Abdul Bahari, Mohd Nazri; Ahmad, Syahida; Tham, Chau Ling; Shaari, Khozirah; Lajis, Nordin H. [Molecules, 2014, vol. 19, # 10, p. 16058 - 16081]

50
[ 1450-74-4 ]
[ 1202-39-7 ]
C₁₇H₁₁Cl₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; trichlorophosphate at 20℃; Cooling with ice;	3.3. General Procedure for the Synthesis of II General procedure: Phosphoryl chloride (POCl3; 20 mmol) was added slowly to a 100 mL SNRB flask containing a mixture of I (5.5 mmol) and the appropriate 2'-hydroxyacetophenone (5 mmol) in pyridine (30 mL). The flask was placed in an ice bath and the reaction mixture was left overnight, with constant stirring at room temperature. The reaction mixture was then poured into 100 mL cold, dilute HCl in a 250 mL EF, followed by extraction with ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The crude product obtained was further purified by open column chromatography.

Reference： [1]Leong, Sze Wei; Mohd Faudzi, Siti Munirah; Abas, Faridah; Mohd Aluwi, Mohd Fadhlizil Fasihi; Rullah, Kamal; Wai, Lam Kok; Abdul Bahari, Mohd Nazri; Ahmad, Syahida; Tham, Chau Ling; Shaari, Khozirah; Lajis, Nordin H. [Molecules, 2014, vol. 19, # 10, p. 16058 - 16081]

51
[ 1450-74-4 ]
[ 14770-88-8 ]
C₁₆H₁₃ClO₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; trichlorophosphate at 20℃; Cooling with ice;	3.3. General Procedure for the Synthesis of II General procedure: Phosphoryl chloride (POCl3; 20 mmol) was added slowly to a 100 mL SNRB flask containing a mixture of I (5.5 mmol) and the appropriate 2'-hydroxyacetophenone (5 mmol) in pyridine (30 mL). The flask was placed in an ice bath and the reaction mixture was left overnight, with constant stirring at room temperature. The reaction mixture was then poured into 100 mL cold, dilute HCl in a 250 mL EF, followed by extraction with ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The crude product obtained was further purified by open column chromatography.

Reference： [1]Leong, Sze Wei; Mohd Faudzi, Siti Munirah; Abas, Faridah; Mohd Aluwi, Mohd Fadhlizil Fasihi; Rullah, Kamal; Wai, Lam Kok; Abdul Bahari, Mohd Nazri; Ahmad, Syahida; Tham, Chau Ling; Shaari, Khozirah; Lajis, Nordin H. [Molecules, 2014, vol. 19, # 10, p. 16058 - 16081]

52
[ 1450-74-4 ]
[ 51557-26-7 ]
C₂₁H₁₅ClO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; trichlorophosphate at 20℃; Cooling with ice;	3.3. General Procedure for the Synthesis of II General procedure: Phosphoryl chloride (POCl3; 20 mmol) was added slowly to a 100 mL SNRB flask containing a mixture of I (5.5 mmol) and the appropriate 2'-hydroxyacetophenone (5 mmol) in pyridine (30 mL). The flask was placed in an ice bath and the reaction mixture was left overnight, with constant stirring at room temperature. The reaction mixture was then poured into 100 mL cold, dilute HCl in a 250 mL EF, followed by extraction with ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The crude product obtained was further purified by open column chromatography.

Reference： [1]Leong, Sze Wei; Mohd Faudzi, Siti Munirah; Abas, Faridah; Mohd Aluwi, Mohd Fadhlizil Fasihi; Rullah, Kamal; Wai, Lam Kok; Abdul Bahari, Mohd Nazri; Ahmad, Syahida; Tham, Chau Ling; Shaari, Khozirah; Lajis, Nordin H. [Molecules, 2014, vol. 19, # 10, p. 16058 - 16081]

53
[ 1450-74-4 ]
[ 23788-74-1 ]
(S)-3-(2-acetyl-4-chloro)phenoxy-1,2-propanediol acetonide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80.0%	With potassium carbonate; In N,N-dimethyl-formamide; at 90℃;	General procedure: Potassium carbonate (4.57 g, 33.09 mmol) and 5-chloro-2-hydroxyacetophenone (5.64 g, 33.09 mmol) were added to a solutionof (S)-3-tosyloxy-1,2-propanediol acetonide (8.24 g,28.78 mmol) in DMF (60 mL). After stirring at 90 C overnight, thereaction mixture was concentrated under vacuum, diluted withethyl acetate, and filtered. The filtrate was concentrated and theresulting oily residue was purified by chromatography on silica gel.Elution with 80/20 cyclohexane/ethyl acetate gave 8.19 g (98.2%) of(R)-37 as a yellow oil:

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 89,p. 252 - 265

54
[ 1450-74-4 ]
[ 23735-43-5 ]
(R)-3-(2-acetyl-4-chloro)phenoxy-1,2-propanediol acetonide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98.2%	With potassium carbonate; In N,N-dimethyl-formamide; at 90℃;	Potassium carbonate (4.57 g, 33.09 mmol) and 5-chloro-2-hydroxyacetophenone (5.64 g, 33.09 mmol) were added to a solutionof (S)-3-tosyloxy-1,2-propanediol acetonide (8.24 g,28.78 mmol) in DMF (60 mL). After stirring at 90 C overnight, thereaction mixture was concentrated under vacuum, diluted withethyl acetate, and filtered. The filtrate was concentrated and theresulting oily residue was purified by chromatography on silica gel.Elution with 80/20 cyclohexane/ethyl acetate gave 8.19 g (98.2%) of(R)-37 as a yellow oil: [a]D25 15.8 (c 1, CHCl3); 1H NMR (CDCl3)d 7.70 (d, 1H, J 2.7 Hz), 7.39 (dd, 1H, J 8.8, 2.7 Hz), 6.90 (d, 1H,J 8.8 Hz), 4.51 (m, 1H), 4.12 (m, 3H), 3.91 (dd, 1H, J 8.5, 5.6 Hz),2.64 (s, 3H), 1.45 (s, 3H), 1.39 (s, 3H).

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 89,p. 252 - 265

55
[ 1450-74-4 ]
[ 613-33-2 ]

Reference： [1]Tetrahedron,2014,vol. 70,p. 6995 - 7005

56
[ 132794-07-1 ]
[ 1450-74-4 ]
2-acetyl-4-chlorophenyl 4-chloro-2,5-difluorobenzoate [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2015,vol. 54B,p. 383 - 390

57
[ 1450-74-4 ]
[ 19219-99-9 ]
[ 64037-24-7 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 8657 - 8667

58
[ 1450-74-4 ]
[ 497-18-7 ]
[ 66108-30-3 ]
N-[1-(5-chloro-2-hydroxyphenyl)ethylidene]-N'-[1-(2-hydroxy-5-methyl-3-nitrophenyl)ethylidene]carbonohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	In ethanol; N,N-dimethyl-formamide; at 225℃; for 9h;	The ligand N-[1-(5-chloro-2-hydroxyphenyl)ethylidene]-N'-[1-(2-hydroxy-5-methyl-3-nitrophenyl)ethylidene] carbonohydrazide was prepared by dropwise addition of equimolar amountsof 5-chloro-2-hydroxy acetophenone (2.4 g, 0.016 mol) to 2-hydroxy-5-methyl-3-nitroacetophenone (3.12 g, 0.016 mol) with stirring at room temperature. This resulting reactionmixture was reacted with a hot ethanol-DMF solution (60:40 v/v; 25 mL) of <strong>[497-18-7]carbohydrazide</strong>(1.44 g., 0.016 mol) and mixture was refluxed on sand bath for about 9 h at 225 oC. The solventwas then partially evaporated in air and faint yellow coloured compound obtained was filteredand washed it with ethanol, petroleum ether and dried in vacuum over anhydrous CaCl2. Thesynthesized ligand was crystallized and conformed though its melting point 313 oC (yield: 72%)and its NMR analysis as follows: 12.68 (S, 1H, OH, phenolic), 14.30 (S, 1H, OH, phenolic),10.19 (S, 1H, imino, NH), 10.23 (S, 1H, imino, NH), 2.12 (S, 3H, Ar-CH3), 2.31 (S, 3H, CH3),2.36 (S, 3H, CH3), 6.91-7.95 (m, 5H, aryl-H). The schematic representation of the synthesis ofligand H2L is shown in Figure 1.

Reference： [1]Bulletin of the Chemical Society of Ethiopia,2015,vol. 29,p. 387 - 397

59
[ 1450-74-4 ]
[ 111841-05-5 ]

Reference： [1]Patent: WO2016/16370,2016,A1

60
[ 1450-74-4 ]
[ 28909-34-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine; hydroxylamine hydrochloride / methanol 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone; triphenylphosphine / dichloromethane

Reference： [1]Current Patent Assignee: TOPHARMAN SHANGHAI CO., LTD.; CHINESE ACADEMY OF SCIENCES; SUZHOU VIGONVITA LIFE SCIENCES; Shanghai Institute of Materia Medica (in: CAS) - CN105399697, 2016, A

61
[ 1450-74-4 ]
[ 3964-52-1 ]
(E)-2-chloro-4-((1-(5-chloro-2-hydroxyphenyl)ethylidene)amino)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	In methanol; for 3h;Reflux;	A 2 mmol hot methanolic (20 ml) solution of 5-chloro-2-hydroxyacetophenone was added in a dropwise manner to a hot methanolic(20 ml) solution of 4-amino-2-chloro phenol (2 mmol). The resultant reaction mixture was refluxed for 3 h leading to the isolation of microcrystalline solid product. The product was filtered and washed with methanol and then finally dried under vacuo over anhydrous calcium chloride. (Scheme 2). Ligand (L2): Yield, 73%, Colour: brown, m.p. >300 C, Anal. Calc. forC14H11NO2Cl2 (%) C, 56.77; H, 3.74; N, 4.72. Found: C, 56.71; H, 3.70; N, 4.68 IR (KBr, cm-1): 1622 nu(HC=N), 3424 nu(OH), 1324 nu(C-O). ESI-MS (m/z+), 297.40.

Reference： [1]Journal of Photochemistry and Photobiology B: Biology,2016,vol. 165,p. 96 - 114

62
[ 1450-74-4 ]
[ 52026-70-7 ]
C₂₀H₁₂ClNO₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With pyridine; trichlorophosphate at 20℃;

Reference： [1]Mahajan, Pravin; Nikam, Mukesh; Asrondkar, Ashish; Bobade, Anil; Gill, Charansingh [Journal of Heterocyclic Chemistry, 2017, vol. 54, # 2, p. 1415 - 1422]

63
[ 99-02-5 ]
[ 1450-74-4 ]
[ 3226-34-4 ]

Yield	Reaction Conditions	Operation in experiment
34%; 6%	With (difluoroboryl)dimethylglyoximatocobalt(II) bis(acetonitrile); water; 3-cyano-1-methylquinolinium cation; In acetonitrile; at 20℃; for 5h;Inert atmosphere; Irradiation; Green chemistry;	1-methyl-3-cyanoquinoline salt as a photosensitizer, cobalt oxime complex 2 as a cobalt catalyst, 5mL of acetonitrile was added2.69 mg (1 × 10 -2 mmol) of photosensitizer and 2.80 mg (6 × 10 -3 mmol) of cobalt catalyst were charged, the atmosphere was replaced with Ar atmosphere, and then0.2 mmol of 3'-chloroacetophenone (R1 is COCH3, R3 is Cl, R2, R4 are independently H) and 2 mmol of H2O are added. Room temperature, high pressureMercury lamp irradiation 5h. After the reaction was completed, the H2 production was detected by GC (TCD) and the conversion of benzene by GC (FID), Then over the column points. Nuclear magnetic resonance spectroscopy and mass spectrometry identification of broad-based as 3 '- chloro -2_ hydroxyacetophenone, 3' - chloro -4_ light base acetophenone and 3 '- chloro-6_Hydroxyacetophenone.The conversion of 3'-chloroacetophenone was 43%. The conversion of 3'-chloro-2-hydroxyacetophenone, 3'-chloro-4-hydroxyacetophenone and 3'-chloro-6-hydroxyacetophenone The yields were 6%, 2% and 34% respectively, and the H2 yield was 42%.

Reference： [1]Patent: CN107324975,2017,A .Location in patent: Paragraph 0126-0127

64
[ 5381-20-4 ]
[ 1450-74-4 ]
C₁₇H₁₁ClO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%	With potassium hydroxide; In ethanol; water; at 20℃;	To a solution of 5'-chloro-2'-hydroxyacetophenone (50 mg, 0.29 mmol) in ethanol (1.5 mL)50% aqueous potassium hydroxide solution (1.5 mL) and thianaphthene-3-carbaldehyde (57 mg, 0.35 mmol) were added and the mixture was stirred at room temperature.Upon completion of the reaction, the reaction mixture was neutralized with 2N hydrochloric acid.The reaction mixture was extracted with ethyl acetate, and the obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.The residue was purified by silica gel column chromatography with hexane-methylene chloride (5: 1), methylene chloride and acetic acid effluent solvent,The fractions containing the desired product were collected and the solvent was distilled off under reduced pressure and then recrystallized from methanol. As a result,Compound [4] (14 mg, 0.043 mmol) was obtained as a yellow solid in 15% yield. The results of 1 H NMR and HRMS of the compound [4] are shown below.

Reference： [1]Patent: JP2017/178941,2017,A .Location in patent: Paragraph 0068

65
[ 1450-74-4 ]
[ 14755-02-3 ]
1-(5-chloro-2-hydroxyphenyl)-3-hydroxy-5-(3-hydroxyphenyl)penta-2,4-dien-1-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 302 - 309

66
[ 1450-74-4 ]
[ 14755-02-3 ]
C₁₇H₁₃ClO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; trichlorophosphate; at 20℃;Cooling with ice;	General procedure: Phosphoryl chloride (POCl3; 20mmol) was added slowly to a 100mL SNRB flask containing a mixture of appropriate cinnamic acid (5.5mmol) and the 2'-hydroxyacetophenone (5mmol) in ice cooled pyridine (30mL) and stirred overnight. The reaction mixture was then poured into 100mL cold, dilute HCl in a 250mL EF, followed by extraction with ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The crude product obtained was further purified by flash chromatography to give cinnamate ester VI.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 302 - 309

67
[ 1450-74-4 ]
[ 92444-99-0 ]
(E)-1-(5-chloro-2-hydroxyphenyl)-3-(2-chloro-5-methylpyridin-3-yl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With sodium hydroxide In ethanol; water at 0 - 20℃;	General procedure for the preparation ofpyridinylchalcones (3a-q) General procedure: 1-(2-Hydroxyphenyl)ethanone 2a (176 mg, 1.29 mmol) and2-chloronicotinaldehyde 1a (200 mg, 1.29 mmol) weredissolved in ethanol (1 ml). Aqueous sodium hydroxide solution (40%, 0.3 ml) was added gradually to the reactionmixture under stirring and the contents were stirred at roomtemperature till starting materials disappeared (TLC). Aftercompletion of the reaction, the solvent was removed underreduced pressure. Cold water was added to the residue,neutralized with cold acetic acid and the reaction mixturewas extracted with ethyl acetate (2 × 20 ml). The organiclayer was washed with brine (2 × 20 ml) and the layers wereseparated. The organic layer was dried over anhydrousNa2SO4 and solvent was removed under reduced pressure.The crude product was purified by column chromatography(EtOAc/hexane) to give pure yellow solid 3a. Similarly,compounds 3b-q were prepared by the reaction of 2-chloronicotinaldehydes 1b-e with substituted 1-(2-Hydroxyphenyl)ethanones 2b-d under optimized conditions.

Reference： [1]Dayakar, Cherupally; Suman, Pathi; Rajkumar, Kommera; Murthy, Thampunuri Ramalinga; Kalivendi, Shasi Vardhan; Raju, Bhimapaka China [Medicinal Chemistry Research, 2018, vol. 27, # 1, p. 80 - 94]

68
[ 14527-42-5 ]
[ 1450-74-4 ]
1-(5-chloro-2-hydroxyphenyl)-3-(thiazol-2-yl)propane-1,3-dione [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 8468 - 8473

69
[ 1450-74-4 ]
[ 57102-98-4 ]
2-acetyl-4-chlorophenyl 9-ethyl-9H-carbazole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With pyridine; trichlorophosphate at 0 - 20℃;	General Procedure for Esterification of Compounds 3(a-e) General procedure: A mixture of compound 1 (1.36 g, 10 mmol) and 9-ethyl-9H-carbazole-3-carboxylic acid 2 (2.3 g, 10 mmol) was dissolv-ed in dry pyridine (10 mL). Cooled the flask in an ice bath and phosphorousoxy chloride (1.53g, 10 mmol) was added dropwise with constant stirring while maintain the temperature between 0-10 °C. After complete addition of phosphorousoxychloride, the reaction mixture was kept overnight at room temperature, then poured over crushed ice and acidified using cold dilute HCl. The off white solid product obtained was filtered and washed with cold dill. NaHCO3 solution followed by washing with cold water. Crude product was dried and recrystallized from ethanol to obtain the desired product in pure form 3(a-e), which gave a positive test for ester.

Reference： [1]Kadnor, Vijay A.; Mhaske, Ganesh R.; Shelke, Sharad N. [Croatica Chemica Acta, 2018, vol. 91, # 3, p. 367 - 375]

70
[ 1450-74-4 ]
[ 52988-34-8 ]
6-chloro-3-hydroxy-2-(4'-methoxy-[1,1'-biphenyl]-4-yl)-4H-chromen-4-one [ No CAS ]

Reference： [1]Bioorganic Chemistry,2019,vol. 89

71
[ 1450-74-4 ]
[ 52988-34-8 ]
C₂₂H₁₇ClO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In methanol; for 3h;Reflux;	General procedure: In a round-bottom flask (25 mL), equipped with magnetic stirrer 2-hydroxyacetophenone (a) (0.2 mL, 1.66 mmol), cumanaldehyde (b) (0.24 g, 1.66 mmol), sodium hydroxide (0.2 g, 5 mmol) and methanol (10 mL) were introduced. The pale yellow mixture was refluxed untilthe color was changed into orange (about 3 h). The reaction mixturewas cooled to room temperature and sodium hydroxide (0.5 N, 10 mL)and then hydrogen peroxide (35%, 0.684 mL) were added. After stirring2-3 h, the mixture was poured into ice-water and the formed precipitatewas filtered to obtain 1 as a yellow solid (75%)

Reference： [1]Bioorganic Chemistry,2019,vol. 89

72
[ 1450-74-4 ]
[ 89763-93-9 ]
6-chloro-2-(2-fluoro-4-(trifluoromethyl)phenyl)-3-hydroxy-4H-chromen-4-one [ No CAS ]

Reference： [1]Bioorganic Chemistry,2019,vol. 89

73
[ 1450-74-4 ]
[ 89763-93-9 ]
C₁₆H₉ClF₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In methanol; for 3h;Reflux;	General procedure: In a round-bottom flask (25 mL), equipped with magnetic stirrer 2-hydroxyacetophenone (a) (0.2 mL, 1.66 mmol), cumanaldehyde (b) (0.24 g, 1.66 mmol), sodium hydroxide (0.2 g, 5 mmol) and methanol (10 mL) were introduced. The pale yellow mixture was refluxed untilthe color was changed into orange (about 3 h). The reaction mixturewas cooled to room temperature and sodium hydroxide (0.5 N, 10 mL)and then hydrogen peroxide (35%, 0.684 mL) were added. After stirring2-3 h, the mixture was poured into ice-water and the formed precipitatewas filtered to obtain 1 as a yellow solid (75%)

Reference： [1]Bioorganic Chemistry,2019,vol. 89

74
[ 5381-20-4 ]
[ 1450-74-4 ]
2-(benzo[b]thiophen-3-yl)-6-chloro-3-hydroxy-4H-chromen-4-one [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 183

75
[ 5381-20-4 ]
[ 1450-74-4 ]
(E)-3-(benzo[b]thiophen-3-yl)-1-(5-chloro-2-hydroxyphenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium hydroxide; In ethanol; water; at 20℃;	General procedure: An aqueous solution of NaOH (3M, 1.6mL) was added to a solution of aromatic ketone (1mmol) and 3-methoxybenzaldehyde (1.2 eq), in EtOH (1-2mL). The reaction was stirred at r.t for 18-24h. The reaction mixture was cooled in an ice-water bath and acidified to pH 2 with concentrated HCl (37%). The solid formed was filtered, washed with ethanol and then further purified by recrystallization from ethanol. When no precipitate occurred, the reaction mixture was extracted with dichloromethane and washed with water and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. Column chromatography was then utilized to purify the desired product.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 183

76
[ 1450-74-4 ]
[ 95-92-1 ]
[ 5006-45-1 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: 5-chloro-2-hydroxyacetophenone; oxalic acid diethyl ester With sodium methylate In 1,4-dioxane; methanol at 120℃; for 0.333333h; Microwave irradiation; Stage #2: With hydrogenchloride In 1,4-dioxane; methanol at 120℃; for 0.666667h; Microwave irradiation;	General Procedure General procedure: The appropriate hydroxyacetophenone (1 or A, 1.16 mmol) was dissolved in dioxane (2 mL) in aMW vial. Then diethyl oxalate (3.49 mmol, 474 μL) and a solution of MeONa in MeOH (2.32 mmol,531 μL, 25% w/w) were added. The resulting solution was heated to 120 °C for 20 min. Then, a solutionof HCl (18 mmol, 3 mL, 6 M) was added and the reaction was heated to 120 °C for 40 min. The reactionwas decanted over water (50 mL) and the solid formed was filtered and washed with water. The solidwas then dried, washed with dichloromethane and dried again.
	Stage #1: 5-chloro-2-hydroxyacetophenone; oxalic acid diethyl ester With methanol; sodium methylate In 1,4-dioxane at 120℃; for 0.333333h; Microwave irradiation; Stage #2: With hydrogenchloride In 1,4-dioxane at 120℃; for 0.666667h; Microwave irradiation;

Reference： [1]Cagide, Fernando; Oliveira, Catarina; Reis, Joana; Borges, Fernanda [Molecules, 2019, vol. 24, # 23]
[2]Angeli, Andrea; Kartsev, Victor; Petrou, Anthi; Pinteala, Mariana; Brovarets, Volodymyr; Slyvchuk, Sergii; Pilyo, Stepan; Geronikaki, Athina; Supuran, Claudiu T. [International Journal of Molecular Sciences, 2021, vol. 22, # 10]

77
[ 1450-74-4 ]
[ 26272-83-3 ]
1-(5-chloro-2-(oxetan-3-yloxy)phenyl)ethan-1-one [ No CAS ]

Reference： [1]Organic Letters,2020,vol. 22,p. 249 - 252

78
[ 1450-74-4 ]
[ 5006-45-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium ethanolate / 1 h / 40 °C 1.2: 16 h / 90 °C 2.1: acetic acid; hydrogenchloride / water / 16 h / Reflux

Reference： [1]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - KR2020/55868, 2020, A

79
[ 1450-74-4 ]
[ 300552-38-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyrrolidine / methanol / 70 °C 2: hydrogenchloride; water / ethyl acetate / 2 h / 20 °C

Reference： [1]Guan, Aiying; Li, Zhinian; Liu, Changling; Yang, Jinlong; Zhang, Pengfei [Journal of Agricultural and Food Chemistry, 2020, vol. 68, # 24, p. 6485 - 6492]

80
[ 1450-74-4 ]
[ 582-24-1 ]
[ 303145-32-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: 5-chloro-2-hydroxyacetophenone With bismuth(lll) trifluoromethanesulfonate In nitromethane at 25℃; for 0.166667h; Green chemistry; Stage #2: 1-phenyl-2-hydroxyethanone In nitromethane at 60℃; for 12h; Green chemistry; chemoselective reaction;

Reference： [1]Chang, Meng-Yang; Chen, Kuan-Ting [Advanced Synthesis and Catalysis, 2021, vol. 363, # 10, p. 2594 - 2609]

81
[ 1450-74-4 ]
[ 102-32-9 ]
[ 108-24-7 ]
3-(4,5-diacetyloxyphenyl)-6-chloro-4-methylchromen-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With triethylamine at 120℃; for 3h;	3.2.1. General Procedure for the Synthesis of Acetyloxy Coumarins (3a-3o) General procedure: A mixture of the appropriate phenylacetic acid (2.83 mmol) and the appropriate2-hydroxyacetophenone (2.97 mmol) in acetic anhydride (3.1 mL) in the presence of triethylamine(8.77 mmol) was refluxed for 3 h. Water was then added, and the mixturewas extracted with dichloromethane, dried over anhydrous Na2SO4, filtered, and concentratedin vacuo to afford the crude products, which on recrystallization from methanol anddichloromethane gave the purified products.

Reference： [1]Deligiannidou, Georgia-Eirini; Detsi, Anastasia; Iliou, Triantafylia; Katopodi, Annita; Kontogiorgis, Christos; Pontiki, Eleni; Tsopelas, Fotios; Tsotsou, Evangelia [Molecules, 2021, vol. 26, # 19]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	1450-74-4	MDL No. :	MFCD00067788
Formula :	C₈H₇ClO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XTGCUDZCCIRWHL-UHFFFAOYSA-N
M.W :	170.59	Pubchem ID :	74061
Synonyms :		Chemical Name :	1-(5-Chloro-2-hydroxyphenyl)ethanone

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:

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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. 1450-74-4 ] {[proInfo.proName]}

Quality Control of [ 1450-74-4 ]

Related Doc. of [ 1450-74-4 ]

Product Details of [ 1450-74-4 ]

Safety of [ 1450-74-4 ]

Application In Synthesis of [ 1450-74-4 ]

[ 1450-74-4 ] Synthesis Path-Upstream 1~28

[ 1450-74-4 ] Synthesis Path-Downstream 1~81

Related Functional Groups of
[ 1450-74-4 ]

Aryls

Chlorides

Ketones

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Yield	Reaction Conditions	Operation in experiment
90%	With aluminum (III) chloride In neat (no solvent) at 140 - 150℃;	p-Chlorophenyl acetate 2c (10 gm, 0.091mol) was in 500 mL round bottom flask containing aluminium chloride (14.56 gm, 0.11 mol). It was heated on an oil bath at 140-150 °C for 5-6 hr. The progress of the reaction was monitored by TLC using ethyl acetate:hexane as a solvent system. The reaction mixture was quenched with crushed ice and obtained solid product was extracted with ethyl acetate (2×50 mL). The organic extracts were washed with brine solution (2×15 mL) and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure to afford the corresponding crude compound. The obtained crude compound 3c was recrystallized using aq. ethanol. Yield 90percent. M.p. 54-56 °C.
87%	at 0 - 20℃; for 16 h;	General procedure: O-Acyloxy benzenes (0.28 mmol) were dissolved in TfOH (3 ml) at 0 °C. The reaction mixture was warmed to room temperature for appropriate time in Table 3, then poured into cold water and ethyl acetate. The organic layer was washed with 1 M HCl, saturated NaHCO₃, and saturated NaCl, and dried over MgSO₄, then filtrated. The filtrate was concentrated and the residue was subjected silica column chromatography to afford acylated products. All spectral data were identical with the literatures.²⁶
60%	at 120 - 160℃;	4-chlorophenyl acetate (2) (0.1 mole) and anhydrous aluminum trichloride (0.11 mole) were mixed thoroughly in a round bottom flask. The reaction mixture was heated gradually at 120°C till HCl gas was completely exhausted. The heating was extended for 2 hours at 160°C. The progress and completion of the reaction was monitored by TLC. At the end of the reaction the resulting aluminum complex was decomposed from crushed ice containing little amount of hydrochloric acid. The crude product was filtered dried and crystallized from methanol. Yield 60percent, m. p. 53-55 °C (Reported m.p. 53°C).

[ CAS No. 1450-74-4 ] {[proInfo.proName]}

Quality Control of [ 1450-74-4 ]

Related Doc. of [ 1450-74-4 ]

Product Details of [ 1450-74-4 ]

Safety of [ 1450-74-4 ]

Application In Synthesis of [ 1450-74-4 ]

[ 1450-74-4 ] Synthesis Path-Upstream 1~28

[ 1450-74-4 ] Synthesis Path-Downstream 1~81

Related Functional Groups of [ 1450-74-4 ]

Aryls

Chlorides

Ketones

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1450-74-4 ]