Hydrochloric Acid → HCID 90410767, compound

Participants

Reaction Conditions

Reaction Steps

In a nitrogen atmosphere, 10.00 g of 3,5-difluoro-1-(4-propylphenyl)benzene was dissolved in 50 mL of THF, and the resultant solution was cooled to −40° C. Then, 30 mL of butyl lithium (1.6 mol/L, hexane solution) was added at such a rate that the inside temperature did not exceed −35° C. After stirring at −40° C. for 1 hour, 5.37 g of trimethoxyborane was added at such a rate that the inside temperature did not exceed −35° C. After stirring at −40° C. for 1 hour, the inside temperature was increased to room temperature, and 10% hydrochloric acid was added until the reaction system became acidic. Then, an organic layer was separated from the mixture, and an aqueous layer was subjected to extraction with toluene. The toluene extract was combined with the organic layer and cooled with ice, and 11.71 g of a 15% aqueous hydrogen peroxide solution was added to the mixture, followed by stirring at room temperature for 15 hours. Further, an organic layer was separated from the mixture, 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 resultant mixture was dried by adding sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was recrystallized from ethanol to yield 10.24 g of 2,6-difluoro-4-(4-propylphenyl)phenol.

Provenance & Evidence