Boron tribromide → HCID 58674650, compound

Participants

Reaction Steps

A solution of (2E)-N-[4-chloro-3-(trifluoromethyl)phenyl]-2-(3-methoxybenzylidene)butanamide (216 mg, 0.54 mmol) in DCM (15 mL) was cooled to 0° C. under an atmosphere of argon. To this solution was added BBr3 (1M in DCM, 1.18 mL). The cooling bath was removed and the reaction mixture was allowed to warm to rt. After stirring for 2 h, the reaction was quenched by the addition of water. The mixture was extracted with EtOAc and the combined organic solutions were washed with water and brine, dried over Na2SO4, filtered, and concentrated. The residue was triturated with DCM and filtered to give the desired phenol (189 mg). 1H NMR (400 MHz, d4-MeOH): δ 8.19 (d, 1H), 7.91-7.87 (dd, 1H), 7.55 (d, 1H), 7.24-7.16 (m, 2H), 6.87-6.85 (m, 2H), 6.77-6.74 (dd, 1H), 2.63 (q, 2H), and 1.14 (t, 3H).

Provenance & Evidence