1-Bromo-4-fluorobenzene → HCID 67391448, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-fluorobromobenzene (0.589 ml, 5.36 mmol) in anhydrous THF (5 ml) at −78° C., under nitrogen, a solution of 2.5 M of BuLi in hexanes (2.1 ml, 5.36 mmol) was added. After stirring the reaction mixture for 1 h at −78° C., a solution of [2-(tert-butyldimethylsilanyloxy)-1(R)-cyclopropylmethylsulfanylmethylethyl]-[2,2-difluoro-2-(4-fluorophenoxy)ethylidene]amine (0.8 g, 1.78 mmol) in THF (5 ml) was added. After stirring for 2 h at −40° C., the reaction mixture was diluted with ethyl ether and the solution was washed with 10% ammonium chloride solution, brine and dried over sodium sulfate. Concentration under vacuum followed by column chromatography over silica gel with ethyl acetate/hexanes (1/10) gave [2-(tert-butyldimethylsilanyloxy)-1(R)-cyclopropylmethylsulfanylmethylethyl]-[2,2-difluoro-2-(4-fluorophenoxy)-1(S)-(4-fluorophenyl)-ethyl]amine (0.75 g, 77%) as an oil.

Provenance & Evidence