Hydrogen Bromide → 2,4'-Difluoro-3-hydroxy-[1,1'-biphenyl]-4-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

48% hydrobromic acid (28.4 mL) was added at room temperature to an acetic acid (150 mL) solution of 2,4′-difluoro-3-methoxybiphenyl-4-carbaldehyde (6.18 g), and the mixture was stirred at 120° C. for 18 hours in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and then, the solvent was distilled off under reduced pressure. The obtained residue was diluted with ethyl acetate and water. The organic layer was separated, and then, the obtained aqueous layer was neutralized with a 1 M aqueous sodium hydroxide solution, followed by extraction with ethyl acetate. Combined organic layers were washed with water and saturated saline in this order and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was passed through a short silica gel column (hexane/ethyl acetate) to obtain the title compound (5.51 g).

Provenance & Evidence