4-(2-BROMO-ACETYL)-BENZOIC ACID METHYL ESTER

4-(2-Bromo-acetyl)-benzoic acid methyl ester (A): To a solution of methyl 4-acetylbenzoate (25 g, 0.14 mol) in 500 mL chloroform was added , drop- wise, bromine (22.42 g, 0.14 mol) in 60 mL chloroform over a period of 3 h. The mixture was stirred over night. Water (200 mL) was carefully added to the reaction mixture, mixed well and the organic layer isolated was washed with saturated sodium hydrogen carbonate in water (200 mL), followed by brine (200 mL), dried over anhydrous sodium sulfate, filtered and filtrate evaporated to get pure product as a light yellow powder (32 g, 89percent).-To a solution of methyl 4-acetylbenzoate (8.91 g, 50.0 mmol) in AcOH (80 mL) was added BrMethyl 4-acetylbenzoate 105 (8.91 g, 50 mmol) was suspended in acetic acid(80 mL) and the mixture was stirred until a clear solution was reached. Then bromine(8.39 g, 52 mmol) was added dropwise to the mixture. The mixture was stirred at room temperature until the strong orange color was disappeared. The solution was cooled toOMethyl 4-acetylbenzoate 105 (8.91 g, 50 mmol) was suspended in acetic acid (80 mL) and the mixture was stirred until a clear solution was reached. Then bromine (8.39 g, 52 mmol) was added dropwise to the mixture. The mixture was stirred at room temperature until the strong orange color was disappeared. The solution was cooled to OTo a solution of 4-acetyl derivative C or E (1.0 equiv.) in chloroform under nitrogen atmosphere and cooled at 0°C, a solution of bromine (1.1 equiv.) in chloroform was added dropwise. The mixture was stirred at 0°C for 30 min, then was allowed to warm to R.T. and stirred for 1H30. The reaction mixture was treated with a saturated aqueous solution of NaHCOMethyl 4-acetylbenzoate (8.0 g, 45.0 mmol, 1.0 eq) was suspended in AcOH (80 mL) and stirred until all solid dissolved. Bromine (8.5 g, 54.0 mmol, 1.2 eq) was added dropwise to the mixture and stirred at rt until all the bromine was consumed. The solution was cooled to 0 °C upon which a precipitate formed which the solid was collected and washed with 50percent aqueous MeOH, dried to give the title compound (8.5 g, yield 74percent) as a white solid.

A phenacyl bromide

Molecular Weight:257.08
XLogP3:2.7
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:255.97351
Monoisotopic Mass:255.97351
Topological Polar Surface Area:43.4
Heavy Atom Count:14
Complexity:219
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes