Boron tribromide → [6-Hydroxy-2-(2-hydroxy-benzyl)-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

Participants

Reaction Steps

Add BBr3 (0.3 mL) dropwise to a stirred solution of [6-methoxy-2-(2-methoxy-benzyl)-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (650 mg, 1.28 mmol) in CH2Cl2 (15 mL) at room temperature. Stir for 1 h and add an additional aliquot of BBr3 (0.2 mL). Continue stirring for 1 h and quench with MeOH and 2-methyl-2-butene. Load the resulting solution on an SCX cartridge, wash with MeOH and elute with 2M NH3/MeOH. Purify the resulting product by flash chromatography (0-5% (2M NH3 in MeOH)/CH2Cl2) to afford [6-hydroxy-2-(2-hydroxy-benzyl)-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (161 mg, 26%).

Provenance & Evidence