Water → HCID 68861339, compound

Participants

Reaction Steps

Boron tribromide (31.8 mL of a 1 M solution in methylene chloride; 31.8 mmol) was added under nitrogen dropwise over 30 minutes to a solution of N-[(3′-bromo-4′-methoxy-1,1′-biphenyl-4-yl)methyl]-2-butyl-N-methyl-1-benzofuran-3-carboxamide (5.37 g, 10.6 mmol), prepared in the previous step, in 150 mL of methylene chloride at dry ice-acetone temperature. After the addition the dry ice-acetone bath was replaced with an ice bath and the stirring continued for 1.5 h. At ice bath temperature-water was added dropwise. The aqueous layer was separated and extracted two times with methylene chloride. The extracts were combined, dried (MgSO4) and the solvent removed under reduced pressure to give N-[(3′-bromo-4′-hydroxy-1,1′-biphenyl-4-yl)methyl]-2-butyl-N-methyl-1-benzofuran-3-carboxamide (5.26 g, 100%) as a light brown foam, MS (ESI) m/z 492 [M+H]+. Elemental Analysis for C27H26BrNO3. Calc'd: C, 65.86; H, 5.32; N, 2.84. Found: C, 64.98; H, 5.15; N, 2.63.

Provenance & Evidence