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[ CAS No. 1009-22-9 ]

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Chemical Structure| 1009-22-9
Chemical Structure| 1009-22-9
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Product Details of [ 1009-22-9 ]

CAS No. :1009-22-9 MDL No. :MFCD00061118
Formula : C8H7BrFNO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :232.05 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1009-22-9 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P280-P305+P351+P338-P311 UN#:2811
Hazard Statements:H301+H311+H331-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1009-22-9 ]

  • Downstream synthetic route of [ 1009-22-9 ]

[ 1009-22-9 ] Synthesis Path-Downstream   1~25

  • 1
  • [ 1009-22-9 ]
  • 2,6-dichloro-3-tributylstannyl-pyridine [ No CAS ]
  • N-[2-(2,6-Dichloro-pyridin-3-yl)-4-fluoro-phenyl]-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% In 1,4-dioxane Heating;
YieldReaction ConditionsOperation in experiment
Aus 2-Brom-4-fluor-acetophenon-oxim, PCl5 in Ae.;
  • 3
  • [ 1003-98-1 ]
  • [ 75-36-5 ]
  • [ 1009-22-9 ]
YieldReaction ConditionsOperation in experiment
89% With triethylamine In dichloromethane at 0 - 20℃;
In ethyl acetate at 80℃; for 0.5h;
With triethylamine In tetrahydrofuran at 0 - 20℃; for 0.666667h; 2.2 General procedure for the preparation of N-(2-bromophenyl)-N-methylacylamides General procedure: The procedure consists of two steps. First, to a stirred, cooled (0-5°C) solution of 2-bromoaniline (2.190g, 10mmol) and Et3N (1.113g, 1.55ml, 11mmol) in 20ml of dry THF, a solution of an appropriate acyl chloride (10mmol) in 5ml of dry THF was added dropwise within 10min. Then the ice bath was removed and the mixture was stirred vigorously for 30min at room temperature. Then, solid Et3NHCl was filtered off and washed with THF (3×5ml). The resulting organic fractions were combined and THF was removed under reduced pressure to yield crude amides. Recrystallization from hexane/CHCl3 and drying in vacuum afforded the analytically pure intermediate compounds: N-(2-bromophenyl)acylamides. In the second step, to a stirred suspension of NaH (0.132g; 5.5mmol) in 5ml of dry THF at 0°C the respective amide (5mmol) dissolved in 10ml of THF was added dropwise within 10min. The reaction mixture was stirred until the solution became clear (30min, hydrogen gas evolved), and the solution of MeI (0.923g; 0.405ml; 6.5mmol) in 5ml of THF was added dropwise within 10min. The solution was warmed up to room temperature and stirred for 3-8h. Then, the reaction mixture was quenched with water (30ml). The resulting solution was extracted with ethyl acetate (3×20ml). Combined organic layers were washed with brine (1×20ml) and dried over Na2SO4. Ethyl acetate was removed under reduced pressure to give crude 1a-r. Recrystallization from hexane and drying in vacuum afforded analytically pure compounds 1a-r. In the case of (1n) and (1o), the same procedure was conducted but instead of MeI, ethyl bromide and benzyl bromide were respectively used. In the case of (1p), 2-bromopyridin-3-amine was used instead of 2 bromoaniline. In the case of (1a-Cl) and (1a-I), the same procedure was conducted but instead 2-bromoaniline, 2-chloro- and 2-iodoaniline were respectively used.
  • 4
  • [ 1009-22-9 ]
  • [ 98-80-6 ]
  • [ 724-20-9 ]
YieldReaction ConditionsOperation in experiment
97% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium phosphate In toluene at 90℃; for 0.333333h;
  • 5
  • [ 1009-22-9 ]
  • 1-(3-fluoro-9H-carbazol-9-yl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 97 percent / Pd(OAc)2; 2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl; K3PO4 / toluene / 0.33 h / 90 °C 2: 95 percent / Pd(OAc)2; molecular sieves 3 Angstroem; Cu(OAc)2 / O2 / toluene / 120 °C
  • 6
  • [ 1009-22-9 ]
  • 2-Chloro-6-fluoro-9H-pyrido[2,3-b]indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 32 percent / Pd(PPh3)4, CuI / dioxane / Heating 2: 63 percent / K2CO3, 18-crown-6 / dimethylformamide / 3 h / 100 °C
  • 7
  • [ 1009-22-9 ]
  • [ 1692-15-5 ]
  • [ 846060-67-1 ]
YieldReaction ConditionsOperation in experiment
80% With sodium carbonate In dimethoxyethane-1,2; water for 3h; Heating / reflux; 9 Example 9 Piperidines of formula III where Q is (iii), and R12 is PHENYL AND R13 is H N- (4-FLUORO-2-PIPERIDIN-4-YL-PHENYL)-ACETAMIDE HYDROCHLORIDE 2-Bromo-4-fluoro-acetanilide (3.00 g, 12.9 mmol) and pyridine-4-boronic acid (1.60 g, 12.9 mmol) are dissolved in 1, 2-DIMETHOXYETHANE (70 ml). Tetrakis (TRIPHENYLPHOSPHINE) palladium (0) (0.89 g, 0.77mmol) is added followed by sodium carbonate (4.10 g, 38.7 mmol) dissolved in water (25 ml). The mixture is heated at reflux for 3 hours, then stirred at ambient temperature overnight. Solvents are evaporated IN VACUO, then ethyl acetate (50ml) and aqueous ammonia (dil. ) are added to the remanence. The phases are separated and the aqueous layer is extracted with ethyl acetate (2 x 50 ml). The combined organic fractions are washed with brine (sat. ), dried (MGS04), filtered and concentrated by means of evaporation. The product is purified by silica gel chromatography eluting with ethyl acetate: heptane: triethylamine (70: 30: 4) followed by ethyl acetate: ethanol : triethylamine (90: 10: 4) to furnish 2.37 g (80%) of the title compound as an oil. LC/MS (M/Z) 231.0 (M+H). 1H NMR (CDCL3) : 2.03 (t, 3H); 6.99 (dd, 1H) ; 7.11 (dt, 1H); 7.28 (dd, 2H); 7.65 (b, 1H, NH); 7.87 (dd, 1H); 8. 62 (dd, 2H).
  • 8
  • [ 1942-45-6 ]
  • [ 1009-22-9 ]
  • [ 865173-53-1 ]
  • [ 865173-54-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; for 1h; 4 N-acetyl-2-Propyl-3-propyl-5-fluoro-indole and 2-Propyl-3-propyl-5-fluoro-1H-indole; A 50 mL three neck flask was charged with palladium acetate (22.4 mg, 0.1 mmol), dtbpf (94 mg, 0.2 mmol), potassium carbonate (690 mg, 5 mmol), 2-bromo-4-fluoro-acetanilide (464 mg, 2 mmol), 4-octyne (264 mg, 2.4 mmol) and NMP (10 mL). The mixture was purged with argon and heated to 130° C. After 1 hr, the reaction mixture was cooled to rt. Ethyl acetate and water were added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic phases were washed with water, brine and dried with MgSO4. Removal of the solvents and purification of the crude by column chromatography afforded a yellow oil as a mixture of the desired product and the corresponding deacelyated indole, in the ratio of 46:54 (407 mg, containing 7.7 wt % AcOEt). The corrected yield was 66%. 1H NMR (400 MHz): δ=7.73 (m, 1H), 7.14 (m, 1H), 6.94 (td, 1H, J=9.2 Hz, J=2.4), 2.94 (t, 2H, J=7.6 Hz), 2.7 (s, 3H), 2.56 (t, 2H, J=7.6), 1.71 (m, 4H), 1.00-0.92 (m, 6H).
  • 9
  • [ 1009-22-9 ]
  • [ 115-19-5 ]
  • [ 877179-01-6 ]
YieldReaction ConditionsOperation in experiment
91% With copper(l) iodide; triethylamine; triphenylphosphine at 85℃; for 6h;
  • 10
  • [ 131112-05-5 ]
  • [ 1009-22-9 ]
  • [ 877179-03-8 ]
YieldReaction ConditionsOperation in experiment
86% With di-tert-butyl(phenyl)phosphonium tetrafluoroborate; bis(acetylacetonato)palladium(II); potassium carbonate In water; butan-1-ol at 60℃; for 13h; Inert atmosphere; Preparation of N-(3',4'-dichloro-5-fluorobiphenyl-2-yl)acetamide General procedure: Under argon, a mixture of aniline or acetanilide (1.0 equivalent), chlorinated diphenylborinic acid (0.5 equivalent) or chlorinated phenylboronic acid (1.0 equivalent), base, [(t-Bu)3PH]BF4 or [(t-Bu)2PhPH]BF4 (0.12 mol %), Pd(acac)2 (0.12 mol %) is heated to 60° C. in 8 ml of water and 2 ml of 1-butanol. The reaction mixture is stirred at 60° C. for about 20 hours, cooled to room temperature and acidified with 1 N hydrochloric acid. After extracting the reaction mixture twice with ethyl acetate, the combined organic phases are dried over magnesium sulphate. The solvent is distilled off under reduced pressure. In accordance with the general procedure, the following biaryls were prepared:
With potassium carbonate; tris[tert-butyl]phosphonium tetrafluoroborate In water; butan-1-ol at 60℃; for 13h; 3 3. Synthesis of N-(3',4'-dichloro-5-fluorobiphenyl-2-yl)acetamide Under argon atmosphere, a suspension of N-(2-bromo-4-fluorophenyl)acetamide (1.00 g, 4.27 mmol), bis(3,4-dichlorophenyl)borinic acid (0.685 g, 2.14 mmol), potassium carbonate (1.03 g, 7.44 mmol), [(t-Bu)3PH]BF4 (1.5 mg, 5 mmol), Pd(acac)2 (1.6 mg, 5 5 mmol) in 8 ml water and 2 ml 1-butanol was heated to 60 °C. The reaction mixture was stirred at 60 °C for about 13 h, cooled to room temperature and acidified with IN HCl. The mixture was extracted twice with ethyl acetate and the organic layer was dried over MgSO4. The solvent was removed under vacuo. After drying 1.22 g raw product was obtained (80.5 % GC-MS-purity, 77 % yield).
With di-tert-butyl(phenyl)phosphonium tetrafluoroborate; palladium(II) acetylacetonate; potassium carbonate In water; butan-1-ol at 60℃; for 13h; Inert atmosphere; Preparation of N- (3',4'-dichloro-5-fluorobiphenyl-2-yl)acetamide N- (2-bromo-4-fluorophenyl) acetamide (1.00 g, 4.27 mmol), bis (3,4-dichlorophenyl) boronic acid (0.685 g, 2.14 mmol) A mixture of potassium carbonate (1.03 g, 7.44 mmol), [(t-Bu) 2 PhhPH] BF4 (1.6 mg, 5.2 μmol) and Pd (acac) 2 (1.6 mg, 5.3 μmol)8 ml of water and 2 ml of 1-butanol was heated to 60 ° C. The reaction mixture was stirred at 60 deg.] C for about 13 hours, cooled to room temperature, acidified with 1N hydrochloric acid. The reaction mixture was extracted twice with ethyl acetate and the combined organic phases were dried over magnesium sulfate. The solvent was distilled off under reduced pressure. 1.21 g of crude product was obtained (90.8 area% HPLC, 86% yield).
  • 11
  • [ 1269988-73-9 ]
  • [ 1009-22-9 ]
  • [ 877179-03-8 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In water; toluene at 82℃; for 19h; Absence of oxygen; 1 Example 1Coupling of N-(2-bromo-4-fluorophenyl)acetamide to sodium tetrakis(3,4-dichlorophenyl)borate in the presence of biphenyl-2-yl(di-tert-butyl)phosphine96 mg [414 μmol] of N-(2-bromo-4-fluorophenyl)acetamide, 71.6 mg [116 μmol] of sodium tetrakis(3,4-dichlorophenyl)borate and 91.3 mg [861 μmol] of sodium carbonate are initially introduced in 0.8 ml of toluene and 0.2 ml of water in the absence of oxygen. 4.76 mg [16 μmol] of biphenyl-2-yl(di-tert-butyl)phosphine (standard solution in toluene) and 9.4 mg [10 μmol] of Pd2 dba3 are added to this mixture. The reaction mixture is stirred for 19 hours at 82° C. After the end of the reaction (HPLC check), the reaction mixture is cooled to RT, 2 ml of acetonitrile are added and filtration is then effected over a nylon filter (pore size 0.45 μm). The HPLC analysis of the mixture gave the following ratio: N-(3',4'-dichloro-5-fluorobiphenyl-2-yl)acetamide:3,3',4,4'-tetrachlorobiphenyl:N-(2-bromo-4-fluorophenyl)acetamide=99.5:0.5:0.
  • 12
  • [ 263879-47-6 ]
  • [ 1009-22-9 ]
  • [ 1268353-92-9 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In water; toluene at 82℃; for 65h; Absence of oxygen; 8 Example 8Coupling of N-(2-bromo-4-fluorophenyl)acetamide to sodium tetrakis(3,4,5-trifluorophenyl)borate in the presence of 1,1-bis(di-tert-butylphosphino)ferrocene106.1 mg [457 μmol] of N-(2-bromo-4-fluorophenyl)acetamide, 66.6 mg [119 μmol] of sodium tetrakis(3,4,5-trifluorophenyl)borate and 87.0 mg [821 μmol] of sodium carbonate are initially introduced in 0.8 ml of toluene and 0.2 ml of water in the absence of oxygen. 8.02 mg [16.9 μmol] of 1,1-bis(di-tert-butylphosphino)ferrocene (standard solution in toluene) and 13 mg [14.2 μmol] of Pd2 dba3 are added to this mixture. The reaction mixture is stirred for 65 hours at 82° C. After the end of the reaction (HPLC check), the reaction mixture is cooled to RT, 2 ml of acetonitrile are added and filtration is then effected over a nylon filter (pore size 0.45 μm). The HPLC analysis of the mixture gave the following ratio: N-(3',4',5'-trifluoro-5-fluorobiphenyl)acetamide:3,3',4,4',5,5'-hexafluorobiphenyl:N-(2-bromo-4-fluorophenyl)acetamide=99.0:1.0:0.
  • 13
  • [ 694-59-7 ]
  • [ 1009-22-9 ]
  • [ 1356388-72-1 ]
YieldReaction ConditionsOperation in experiment
55% With di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; palladium diacetate; potassium carbonate In toluene at 140℃; Microwave irradiation; Sealed vessel; General Procedure for the Preparation of 2-(2-Acetamidoaryl)pyridine 1-Oxides (4). General procedure: In either a 10-mL or an 80-mL CEM microwave vessel equipped with a teflon stir bar, an appropriate obromoacetalilide(3, 0.6 mmol in the 10-mL vessel or 3 mmol in the 80-mL vessel, 1 equiv) was added to a stirred mixture of toluene (3.3 ml/mmol 5), pyridine N-oxide (4 equiv), palladium acetate (5 mol %), di-tert-butylmethylphosphonium tetrafluoroborate (15 mol %), and anhydrous potassium carbonate (2 equiv). The mixture was sealed and heated to 140 °C (110 °C for compound 3h) in a CEM/Discover Benchmate single-mode microwave reactor with an external IR temperature sensor. For those procedures conducted in the 10-mL vessel, the reaction was heated to the required temperature over a period of < 5 min. For those procedures conducted in the 80-mL vessel, the reaction was heated to the required temperature stepwise over a period of 15 minutes. The reaction mixture was held at 140 °C (110 °C for compound 3h) for 1 hr (10-mL vessel) or 3 hr (80-mL vessel). The mixture was cooled to room temperature and filtered through a Celite pad which was washed with acetone-dichloromethane (1:1). The combined filtrate and washings were evaporated in vacuo and the residue purified by flash column chromatography on silica gel (acetone-dichloromethane mixtures) to give the product.
  • 14
  • [ 1009-22-9 ]
  • [ 106-96-7 ]
  • [ 1527494-44-5 ]
YieldReaction ConditionsOperation in experiment
88% With triethylbutylammonium chloride; potassium hydroxide In tetrahydrofuran; toluene at 20℃; for 20h;
  • 15
  • [ 1009-22-9 ]
  • [ 1527494-49-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide; triethylbutylammonium chloride / toluene; tetrahydrofuran / 20 h / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; tetrabutylammonium acetate / 1,4-dioxane / 1 h / 60 °C
  • 16
  • [ 1009-22-9 ]
  • [ 1527494-52-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide; triethylbutylammonium chloride / toluene; tetrahydrofuran / 20 h / 20 °C 2: palladium diacetate; triphenylphosphine; tetrabutylammonium acetate / N,N-dimethyl-formamide / 16 h / 100 °C
  • 17
  • [ 1009-22-9 ]
  • [ 1527494-52-5 ]
  • [ 1527494-55-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium hydroxide; triethylbutylammonium chloride / toluene; tetrahydrofuran / 20 h / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; tetrabutylammonium acetate / 1,4-dioxane / 1.5 h / 60 °C 3: palladium diacetate; triphenylphosphine; potassium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C / Microwave irradiation
  • 18
  • [ 1009-22-9 ]
  • [ 1527494-54-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide; triethylbutylammonium chloride / toluene; tetrahydrofuran / 20 h / 20 °C 2: palladium diacetate; triphenylphosphine; tetrabutylammonium acetate / N,N-dimethyl-formamide / 16 h / 100 °C
  • 19
  • [ 1009-22-9 ]
  • [ 1527494-54-7 ]
  • C25H22FNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium hydroxide; triethylbutylammonium chloride / toluene; tetrahydrofuran / 20 h / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; tetrabutylammonium acetate / 1,4-dioxane / 1 h / 60 °C 3: palladium diacetate; triphenylphosphine; potassium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C / Microwave irradiation
  • 20
  • [ 1009-22-9 ]
  • [ 1527494-55-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium hydroxide; triethylbutylammonium chloride / toluene; tetrahydrofuran / 20 h / 20 °C 2: palladium diacetate; triphenylphosphine; tetrabutylammonium acetate / N,N-dimethyl-formamide / 16 h / 100 °C 3: potassium hydroxide / water; tetrahydrofuran / 5 h / 40 °C
Multi-step reaction with 4 steps 1: potassium hydroxide; triethylbutylammonium chloride / toluene; tetrahydrofuran / 20 h / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; tetrabutylammonium acetate / 1,4-dioxane / 1.5 h / 60 °C 3: palladium diacetate; triphenylphosphine; potassium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C / Microwave irradiation 4: potassium hydroxide / water; tetrahydrofuran / 5 h / 40 °C
  • 21
  • [ 1009-22-9 ]
  • [ 1527494-47-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide; triethylbutylammonium chloride / toluene; tetrahydrofuran / 20 h / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; tetrabutylammonium acetate / 1,4-dioxane / 1.5 h / 60 °C
  • 22
  • [ 1009-22-9 ]
  • [ 411235-57-9 ]
  • N-(2-cyclopropyl-4-fluoro-phenyl)-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With potassium phosphate; palladium diacetate; tricyclohexylphosphine In water; toluene at 100℃; for 16h; Inert atmosphere; Step 2: To a stirred solution of N-(2-bromo-4-fluoro-phenyl)-acetamide (65.0 g, 0.28 mol) in a mixture of toluene- water (1 : 1, 1.3 L) was added tricyclohexyl phosphine (7.85 g, 0.03 mol) followed by the addition of K3PO4 (208.2 g, 0.98 mol) at ambient temperature. This mixture was then degassed with Ar for 30 minutes. cyclopropyl boronic acid (31.2 g, 0.37 mol) followed by Pd(OAc)2 (3.2 g, 0.01 mol) was added and the reaction mixture was heated ot 100 °C for 16 h. After consumption of the starting material (monitored by TLC, 20% EA-Hexane, Rf 0.4) the reaction mixture was cooled to ambient temperature, diluted with EtOAc (1 L), washed with water (2 x 500 ml) followed by brine (500 ml) and was then dried over anhydrous Na2SC>4 and concentrated under reduced pressure to afford the crude compound. The obtained crude compound was purified by column chromatography (100-200 mesh silica gel and 15-20% EtOAc/hexane as eluent) to afford N-(2-cyclopropyl-4-fluoro-phenyl)-acetamide (51.5 g, 95%) as a brownish solid.
95% Stage #1: N-(2-bromo-4-fluorophenyl)acetamide With potassium phosphate; tricyclohexylphosphine In water; toluene at 20℃; for 0.5h; Inert atmosphere; Stage #2: cyclopropylboronic acid With palladium diacetate In water; toluene at 100℃; for 16h; Inert atmosphere; Step 2 To a stirred solution of N-(2-bromo-4-fluoro-phenyl)-acetamide (65.0 g, 0.28 mol) in a mixture of toluene- water (1:1, 1.3 L) was added tricyclohexyl phosphine (7.85 g, 0.03 mol) followed by the addition of K3PO4 (208.2 g, 0.98 mol) at ambient temperature. This mixture was then degassed with Ar for 30 minutes. Cyclopropyl boronic acid (31.2 g, 0.37 mol) followed by Pd(Oac)2 (3.2 g, 0.01 mol) was added and the reaction mixture was heated ot 100 °C for 16 h. After consumption of the starting material (monitored by TLC, 20% EA-Hexane, Rf 0.4) the reaction mixture was cooled to ambient temperature, diluted with EtOAc (1 L), washed with water (2 x 500 ml) followed by brine (500 ml) and was then dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude compound. The obtained crude compound was purified by column chromatography (100-200 mesh silica gel and 15- 20% EtO Ac/hexane as eluent) to afford N-(2-cyclopropyl-4-fluoro-phenyl)-acetamide (51.5 g, 95%) as a brownish solid.
With potassium phosphate; tricyclohexylphosphine In water; toluene at 100℃; for 6h; Sealed tube; Inert atmosphere; Microwave irradiation; 15.1 Step 1: N-(2-Cyclopropyl-4-fluorophenyl)acetamide A mixture comprising N-(2-bromo-4-fluorophenyl)acetamide (1 g, 4.31 mmol), cyclopropylboronic acid (0.481 g, 5.60 mmol), tricyclohexylphosphine (0.121 g, 0.431 mmol), potassium phosphate (tribasic) (3.20 g, 15.08 mmol), toluene (10 ml) and water (10 ml) was equally divided between two 10-20 ml microwave tubes. Each reaction tube was sealed, evacuated and filled with nitrogen (3×) and placed in the microwave at 100° C. for 6 hrs. The contents of the vials were combined, diluted with EtOAc and the layers separated. The organic extracts were washed with water (2×), dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound as a brown solid. The product was used crude in the next step. (0551) LC-MS: Rt 0.88 mins; MS m/z 194.3 [M+H]+; Method 2minLowpHv01
  • 23
  • [ 351-83-7 ]
  • [ 1009-22-9 ]
YieldReaction ConditionsOperation in experiment
96% With NBS In acetonitrile for 2h; Irradiation; regioselective reaction;
89% With NBS; silver hexafluoroantimonate; copper (II) acetate; [CpA5RhCl2]2 In 1,2-dichloro-ethane at 20℃; for 18h; Schlenk technique; Inert atmosphere; regioselective reaction;
87% With NBS; bis[dichlorido(η5-1,2,3,4,5-pentamethyl-cyclopentadienyl)iridium(III)]; <i>N</i>-<i>tert</i>-butoxycarbonyl-<i>L</i>-phenylalanine; silver(I) bis(trifluoromethanesulfonyl)imide In 1,2-dichloro-ethane at 20℃; for 4h; Inert atmosphere; Sealed tube;
87% With acetic anhydride; copper(II) bis(trifluoromethanesulfonate); N-(benzenesulfonyl)-N-fluorobenzenesulfonamide; sodium bromide In acetonitrile at 80℃; Inert atmosphere; regioselective reaction;
79% With NBS; methanesulfonic acid; NiCl2·6H2O In lithium hydroxide monohydrate at 20℃; for 5h; Sealed tube; Microwave irradiation; Green chemistry; regioselective reaction; Procedure B General procedure: A 10 mL microwave vial was charged with an anilide or carbamate derivative (1.0 equiv, 0.5 mmol), NXS (1.2 equiv, 0.6 mmol), Ag2CO3 (10 mol%, 14 mg), MSA (3.0 equiv, 1.5 mmol, 144 mg) and toluene (2.0 mL). The vial was then sealed and stirred at 50 °C, for 8 h. After the reaction time, the mixture was diluted with EtOAc and washed with sodium bicarbonate solution. The organic layer was dried with anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (n-hexane/EtOAc) to give the desired product.
633 kg With bromine at 10 - 15℃; for 3h; Large scale; 1.4; 2.4 (4) Put 1600kg of compound C into the reactor, cool down to 10-15°C, add 400kg of bromine dropwise, pay attention to the absorption of exhaust gas during the dropwise addition, keep the reaction for 3h after the dropwise addition, add 500kg of water, stir, stand for stratification, The organic layer was washed with an aqueous solution of sodium bisulfite, allowed to stand, and the layers were separated. The dichloromethane layer was concentrated to substantially no fractions, 1700 kg of methanol was added, the temperature was increased to dissolve, the temperature was lowered to 0-5 °C for crystallization for 1 h, suction filtration, centrifugation, and drying. 633kg of o-bromo-p-fluoroacetylaniline was obtained by drying, and the purity was 98.8%.

  • 24
  • [ 371-40-4 ]
  • [ 1009-22-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloromethane / 20 °C / Inert atmosphere 2: bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; <i>N</i>-<i>tert</i>-butoxycarbonyl-<i>L</i>-phenylalanine; silver(I) triflimide; N-Bromosuccinimide / 1,2-dichloro-ethane / 4 h / 20 °C / Inert atmosphere; Sealed tube
  • 25
  • [ 351-83-7 ]
  • [ 1009-22-9 ]
  • [ 392-14-3 ]
YieldReaction ConditionsOperation in experiment
56% With N-Bromosuccinimide; cobalt acetylacetonate; trifluoroacetic acid; silver(l) oxide In 1,2-dichloro-ethane at 60℃; for 16h; Overall yield = 70 %; regioselective reaction;
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