Ethyl Acetate → 2-broMo-5-hydroxybenzoic acid Methyl ester

Participants

Reaction Steps

To a solution of compound methyl 2-bromo-5-methoxybenzoate (100 g, 410 mmol) in DCM (2000 mL) was added and BBr3 (1N, 150 mL) at −78° C. under N2 The mixture was stirred at 0° C. under N2 for 24 hr. The reaction was quenched with MeOH (500 mL), concentrated to dryness, diluted with H2O (50 mL), and extracted with ethyl acetate (800 mL*3), The organic phase was washed with saturated sodium bicarbonate solution 50 mL, dried over Na2SO4. After concentration, the crude product was purified by silica gel chromatography eluted with PE:EA=1:1 to give title product (80 g, 85% yield) as yellow oil. LCMS (10-80 AB—2MIN.M): Rt=0.820, purity=85%, M+1=231.

Provenance & Evidence