Hydrochloric Acid → 3-Fluoro-4′-propyl[1,1′-biphenyl]-4-ol

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Reaction Conditions

Reaction Steps

In a nitrogen atmosphere, 44.32 g of 3-fluoro-1-(4-propylphenyl)benzene was dissolved in 220 mL of THF, the resultant solution was cooled to −74° C., and 210 mL of secondary butyl lithium (1.0 mol/L, hexane solution) was added at such a rate that the inside temperature did not exceed −60° C. After stirring at −74° C. for 1 hour, 23.64 g of trimethoxyborane was added at such a rate that the inside temperature did not exceed −60° C. After stirring at −74° C. for 1 hour, the inside temperature was increased to room temperature, and 10% hydrochloric acid was added until the system became acidic. Then, an organic layer was separated, and an aqueous layer was subjected to extraction with toluene. The toluene extract was combined with the organic layer and cooled with ice, and 54 g of a 15% aqueous hydrogen peroxide solution was added to the mixture, followed by stirring under ice cooling for 3 hours. Further, an organic layer was separated, and an aqueous layer was subjected to extraction with toluene. The toluene extract was combined with the organic layer and washed with a 10% aqueous sodium sulfite solution and saturated brine. The organic layer mixture was dried by adding sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was recrystallized from hexane to yield 41.01 g of 2-fluoro-4-(4-propylphenyl)phenol.

Provenance & Evidence