Water → 4-Bromo-2-(4-fluorophenyl)-3-(pyridin-4-yl)thiophene

Participants

Reaction Conditions

Reaction Steps

4,5-Dibromo-2-(4-fluorophenyl)-3-(pyridin-4-yl)thiophene (13.88 g (33.6 mmol), prepared as described in 4)) was dissolved in tetrahydrofuran (140 ml). To the solution was added dropwise at −78° C. a solution of 1.59 M butyl lithium/hexane (23.3 ml, 37 mmol). The resulting mixture was stirred at −78° C. for 15 minutes. At the end of this time, water (24 ml) was added to the reaction mixture and it was allowed to warm to room temperature. The reaction mixture was partitioned between a saturated aqueous solution of ammonium chloride and ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The residue (solid) was washed with diethyl ether, to give the title compound (11.20 g) as a pale brown powder (yield quantitative).

Provenance & Evidence