Boron tribromide → HCID 10275168, compound

Participants

Reaction Steps

N-[(4-Dimethylaminophenyl)methyl]-N-(4-isopropylphenyl)-7-methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxamide (3.2 g) was dissolved in methylene chloride (60 mL), and boron tribromide (0.72 mL) was added under ice-cooling. The mixture was stirred at room temperature for one day. The reaction mixture was partitioned between saturated aqueous sodium hydrogencarbonate and chloroform. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give N-[(4-dimethylaminophenyl)methyl]-7-hydroxy-N-(4-isopropylphenyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.36 g). melting point: 214-217° C.

Provenance & Evidence