Boron tribromide → trans-4-Hydroxystilbene

Participants

Reaction Conditions

Reaction Steps

To 210 mg (1 mmol) of (E)-4-methoxystilbene (4b) in 7 mL of CH2Cl2 was added 1.28 mL of 1M BBr3 (1.3 mmol) in dichloromethane at −10° C. The mixture was stirred for 4 h at −5° C. and quenched by pouring into cold water. The product was extracted with CH2Cl2, dried over anhydrous MgSO4 and chromatographed using 1:10 CH3OH:CH2Cl2 to afford 85 mg (43%) of 4a. mp 184-185° C.

Provenance & Evidence