4-Bromo-2-fluorobenzoic acid ethyl ester

Step 1.A) ethyl 4-bromo-2-fluorobenzoate [0880] To a solution of 4-bromo-2-fluorobenzoic acid (3.0 g) in ethanol (20 mL) was added thionyl chloride (2.0 mL) at 0°C, and the mixture was stirred overnight at 70°C. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution, the mixture was concentrated under reduced pressure, and the residue was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (3.30 g). Compound 4-bromo-2-fluoro-benzoic acid (2g, 9.1mmoL) was dissolved in 20mL of ethanol was added 2mL of concentrated sulfuric acid and refluxed overnight, then rotating the ethanol with sodium bicarbonate to about pH = 8, ethyl ester extraction, the organic phase spin dry vested 2g product. The above product (100mg, 0.4mmol) and piperazine (40mg, 0.48mmol) were mixed in 5mL of toluene, under nitrogen, was added successively cesium carbonate (188mg, 0.6mmoL), 10mg of bis (tri-t-butylphosphine) palladium, followed by stirring at 130 microwave 6 hours, and then distilled toluene, was added 20mL of water and 20mL of dichloromethane, the organic phase was dried over sodium sulfate, filtered, and the filtrate worked spin column to give 2-fluoro-4- (piperazin - 1- yl) benzoic acid ethyl ester (35mg).Step 1.A) ethyl 4-bromo-2-fluorobenzoate [0880] To a solution of 4-bromo-2-fluorobenzoic acid (3.0 g) in ethanol (20 mL) was added thionyl chloride (2.0 mL) at 0°C, and the mixture was stirred overnight at 70°C. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution, the mixture was concentrated under reduced pressure, and the residue was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (3.30 g). Compound 4-bromo-2-fluoro-benzoic acid (2g, 9.1mmoL) was dissolved in 20mL of ethanol was added 2mL of concentrated sulfuric acid and refluxed overnight, then rotating the ethanol with sodium bicarbonate to about pH = 8, ethyl ester extraction, the organic phase spin dry vested 2g product. The above product (100mg, 0.4mmol) and piperazine (40mg, 0.48mmol) were mixed in 5mL of toluene, under nitrogen, was added successively cesium carbonate (188mg, 0.6mmoL), 10mg of bis (tri-t-butylphosphine) palladium, followed by stirring at 130 microwave 6 hours, and then distilled toluene, was added 20mL of water and 20mL of dichloromethane, the organic phase was dried over sodium sulfate, filtered, and the filtrate worked spin column to give 2-fluoro-4- (piperazin - 1- yl) benzoic acid ethyl ester (35mg).

Molecular Weight:247.06
XLogP3:2.9
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:245.96917
Monoisotopic Mass:245.96917
Topological Polar Surface Area:26.3
Heavy Atom Count:13
Complexity:187
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes