Boron tribromide → 4-[5-(4-Hydroxyphenyl)thiazol-2-yl]benzoic acid

Participants

Reaction Steps

To a solution of boron tribromide (1.0M in dichloromethane, 97.7 ml) was added dropwise methyl 4-[5-(4-methoxyphenyl)thiazol-2-yl]benzoate (3.18 g) in dichloromethane (50 ml) at −78° C. The reaction mixture was allowed to warm to room temperature, and stirred for 2 hours. The reaction mixture was poured into ice-water (1000 ml), and stirred for 30 minutes at room temperature. The precipitate was collected by filtration, washed with water, and dried overnight to give in the proportion of 37:63 mixture of methyl 4-[5-(4-hydroxyphenyl)thiazol-2-yl]benzoate and 4-[5-(4-hydroxyphenyl)thiazol-2-yl]benzoic acid (3.07 g), and those were used without purification in the next reaction.

Provenance & Evidence