Boron tribromide → N-Trifluoroacetyl-8-bromo-7-hydroxy-1-isopropyl-2,3,4,5-tetrahydro-1H-3-benzazepine

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Reaction Steps

A solution of N-trifluoroacetyl-8-bromo-1-isopropyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine (0.041 g, 0.10 mmol) in dichloromethane (1 mL) was treated with BBr3 (0.32 ml, 1.0 M solution in CH2Cl3) and stirred overnight at 20 C. The excess BBr3 is quenched with water and the resulting mixture diluted with ether (50 mL), washed twice with saturated aqueous Na2CO3 (20 mL) and concentrated. Flash chromatography (20% EtOAc in hexanes, silica) resulted in 0.037 g clear oil. MS calculated for C15H17BrF3NO2+H: 380, observed: 380.

Provenance & Evidence