Boron tribromide → 2-Methyl-1,3-benzothiazol-6-ol

Participants

Reaction Steps

To a cooled (−78° C.) solution of 6-methoxy-2-methylbenzo[d]thiazole (0.861 g, 4.80 mmol) in dichloromethane (10 mL) was added BBr3 (5 mL of 1.0 M solution in dichloromethane). After slowly warming to room temperature and stirring for 16 hours, the mixture was cooled to 0° C. and slowly quenched with methanol (20 mL). The reaction mixture was warmed to room temperature and concentrated under reduced pressure. The residue was partitioned between saturated NaHCO3 and dichloromethane/isopropyl alcohol (85/15). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to provide the crude product (0.351 g, 44%) that was used without further purification.

Provenance & Evidence