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

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.

1. washthe reaction mixture was washed with 1N HCl, saturated NaHCO3, water, brine
2. dry with materialdried over anhydrous sodium sulfate
3. stirringThe reaction mixture was stirred at 55° C. overnight
4. filtrationfiltered
5. washthe solid washed with acetone
6. concentrationThe filtrate was concentrated
7. dissolutiondissolved in Et2O (100 mL)
8. washwashed with water, brine
9. dry with materialdried over anhydrous sodium sulfate

ORD record

ord-7d4c2fb836c842c99764c9907a4da2e0

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08853250B2