1-bromo-3-(2,2,2-trifluoroethoxymethyl)benzene

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under nitrogen atmosphere, a suspension of sodium hydride (352 mg, 60 wt. % oil dispersion) in tetrahydrofuran (10 ml) was cooled to 0° C., 2,2,2-trifluoroethanol (0.63 ml) was added thereto, and the mixture was stirred for 5 minutes. Then, 3-bromobenzyl bromide (2.00 g) was added thereto, and then the mixture was stirred at reflux for 1 hour. This reaction mixture was cooled to room temperature, a saturated aqueous solution of ammonium chloride was added thereto, and the mixture was extracted with ethyl acetate. This organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/0 to 10/1) to give the titled compound (2.05 g). the mixture was stirred at reflux for 1 hour This reaction mixture was cooled to room temperature the mixture was extracted with ethyl acetate This organic layer was washed with a saturated aqueous solution of sodium chloride dried over anhydrous sodium sulfate concentrated under reduced pressure The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/0 to 10/1)