Acetone → 1-(2-Iodoethyl)-4-(trifluoromethyl)benzene

Participants

Reaction Steps

To 4-(trifluoromethyl)phenyl alcohol (5.0 g, 0.026 mol) in methylene chloride (30 mL, 0.5 mol) at 0° C. was added triethylamine (5.13 mL, 0.0368 mol) followed by methanesulfonyl chloride (3.92 g, 0.0342 mol). After stirring from 0° C. to room temperature for 3 hours, the reaction mixture was washed with 1N HCl, saturated NaHCO3, water, brine and dried over anhydrous sodium sulfate. To the crude product in acetone (50 mL, 0.7 mol) was added sodium iodide (5.9 g, 0.039 mol). The reaction mixture was stirred at 55° C. overnight, filtered and the solid washed with acetone. The filtrate was concentrated, dissolved in Et2O (100 mL), washed with water, brine and dried over anhydrous sodium sulfate to give 7.51 g of brown liquid.

Provenance & Evidence