Sodium Hydroxide → 3′,4′,5′-Trifluoro-2-nitro-1,1′-biphenyl

Participants

Reaction Steps

To a solution of 500 mg (1.49 mmol) of 3,4,5-trifluoro-1-(6-bromo-6-nitrocyclohex-3-en-1-yl)-benzene from example 2.4 in 10 ml of toluene were added 200 mg (0.6 mmol) of tetrabutylammonium bromide and 15 ml of aqueous NaOH (4M) and the mixture was stirred for 24 h at room temperature. During the reaction, air was sparged through the mixture. Then the reaction mixture was stirred for another 12 h at 50° C. After cooling to room temperature, the phases were separated, the aqueous phase was extracted with ethylacetate (3×10 ml) and the organic phases were dried over Na2SO4. Column chromatography (SiO2, cyclohexane/ethylacetate 8:1) yielded 218 mg (0.86 mmol, 58% of theory) of the title compound as a reddish solid.

Provenance & Evidence