Bromine → 3'-Bromo-4'-methoxy-1,1'-biphenyl-4-carbaldehyde

Participants

Reaction Steps

Bromine (8.2 mL, 0.160 mol) in 40 mL of glacial HOAc was added under nitrogen dropwise over 30 minutes to a solution of 4′-methoxy-1,1′-biphenyl-4-carbaldehyde (31.0g, 0.146 mol), prepared in the previous step, in 500 mL of glacial HOAc at room temperature. After the addition the reaction was stirred at room temperature for 16 h. During the reaction a solid precipitated. The solid can be collected by filtration. If by TLC starting material remains in either the solid or filtrate the solid can be redissolved and additional bromine added until the reaction is complete. When the reaction is complete by TLC, water is added and the solid present is collected by filtration to give 3′-bromo-4′-methoxy-1,1′-biphenyl-4-carbaldehyde (40.8 g, 96%) as a white solid, MS (ESI) m/z 290. Elemental Analysis for C14H11BrO2. Calc'd: C, 57.76; H, 3.81; N, 0.00. Found: C, 57.30; H, 3.61; N, 0.00.

Provenance & Evidence