5-Bromo-2-methylphenol

39478-78-9

36138-76-8

General procedure for the synthesis of 5-bromo-2-methylphenol from 2-amino-4-bromotoluene: A solution of concentrated sulfuric acid (6 mL) in distilled water (75 mL) was added to 5-bromo-2-methylaniline (1 g, 5.38 mmol). The resulting suspension was heated to 90 °C and stirred for 4.5 hours. Subsequently, the reaction mixture was cooled to 0 °C using an ice bath and a solution of sodium nitrite (384 mg, 5.57 mmol) in water (5 mL) was slowly added at this temperature. After addition, the reaction mixture was allowed to gradually warm up to room temperature. Next, the reaction mixture was poured into a solution of concentrated sulfuric acid (6 mL) in water (75 mL) preheated to 90°C. Stirring of the reaction mixture was continued at 90 °C for 1 hour, then the heating was stopped and it was allowed to cool naturally and stand overnight. A precipitate was observed to form from the reaction mixture. The precipitate was collected by filtration, washed with water and dried in a vacuum oven to give 5-bromo-2-methylphenol as a final brown solid (510 mg, 2.73 mmol, 51% yield). The mass spectrum (ESI) showed m/z of 185 and 187 [M-H]