Methyl 3-broMo-4-carbaMoylbenzoate synthesis

Yield:1149388-50-0 100%

Reaction Conditions:

with dihydrogen peroxide;potassium carbonate in water;dimethyl sulfoxide at 20; for 18.5 h;

Steps:

44.1

STEP 1 : Methyl 3-bromo-4-cyanobenzoate (prepared as described in Wang, G. T. et al. Bioorg. Med. Chem. Lett. 2005, 15(1), 153) (130 mg, 0.54 mmol) was dissolved in DMSO (1.5 mL) and was cooled in a cold water bath. 30% aqueous hydrogen peroxide (0.1 mL) and potassium carbonate (23.9.0 mg, 0.17 mmol) were added and the mixture was stirred at room temperature for 18.5 h. The reaction mixture was partitioned between ethyl acetate and 10% aqueous lithium chloride. The aqueous portion was extracted with ethyl acetate. The combined organic portions were dried over sodium sulfate, filtered and concentrated to afford methyl 3-bromo-4- (aminocarbonyl)benzoate (quantitative yield) as a yellow oil. GCMS for CgH₈BrNO₃: 257, 259 (M⁺).

References:

WO2009/55077,2009,A1 Location in patent:Page/Page column 446