Sulfuric Acid → 2-broMo-5-hydroxybenzoic acid Methyl ester

Participants

Reaction Conditions

Reaction Steps

Compound of example 151 (12 g, 52.1 mmol) was added to 10% aqueous sulfuric acid (110 mL) at 0° C. An aqueous solution (40 mL) of NaNO2 (4.3 g, 62.32 mmol) was added dropwise, with stirring at 0-5° C. The reaction mixture was stirred for 10 min. and was added to an ice cold aqueous solution of copper sulfate (156 g, 1 L, 625 mmol) containing Cu2O (6.8 g, 47.55 mmol). The resultant mixture was stirred at 0° C. for 10 min. It was diluted with water and extracted using EtOAc (3×500 mL). The organic extract was washed with water, dried (anhydrous Na2SO4), concentrated and purified using a silica gel column and 2% EtOAc in petroleum ether (60-80° C.) as eluant to obtain the title compound.

Provenance & Evidence