Boron tribromide → 2,6-Dichloro-4-hydroxybenzoic acid

Participants

Reaction Conditions

Reaction Steps

2,6-Dichloro-4-methoxy-benzoic acid (500 mg, 2.3 mmol) was taken up in CH2Cl2 and cooled to −78° C. BBr3 (6.9 ml of a 1 M solution in CH2Cl2) was added to the solution at −78° C. The solution was warmed to 25° C. and stirred at that temperature for 16 h. The solution was quenched with 3 N NaOH. The aqueous layer was extracted with CH2Cl2. The aqueous layer was cooled (0° C.) and acidified with conc. HCl (pH=1-2). The aqueous layer was extracted with CH2Cl2. The combined organic layers were dried (Na2SO4). Filtration and concentration gave the crude phenol which was used without further purification.

Provenance & Evidence