Boron tribromide → 2-Hydroxy-N-[3-hydroxy-4-(6-hydroxy-1,3-benzothiazol-2-yl)phenyl]-5-(trifluoromethoxy)benzamide

Participants

Reaction Steps

Prepared as described in the Demethylation section using 2-methoxy-N-[3-methoxy-4-(6-methoxy-1,3-benzothiazol-2-yl)phenyl]-5-(trifluoromethoxy)benzamide (0.30 g, 0.595 mmol) in dry DCM (12 ml) and BBr3 (1.0M in DCM, 1.9 ml, 1.9 mmol) at −78° C. under an atmosphere of argon. Additional BBr3 (1.0 M in DCM, 1.9 ml, 1.9 mmol) was added dropwise and the reaction mixture stirred at room temperature for 4 d to give the title compound (88 mg, 32%) as a pale yellow solid after work-up and flash chromatography (4:2:0.3 Hexane/EtOAc/MeOH).

Provenance & Evidence