Trichloroacetamide

• 2-Phenylethyl Alcohol [P0084]
• Trichloroacetamide [T0368]
• Triphenylphosphine [T0519]
• Dichloromethane

To a mixture of 2-phenylethyl alcohol (0.196 mL, 1.64 mmol) and PPh₃ (0.859 g, 3.27 mmol) in CH₂Cl₂ (8.2 mL) at r. t. was added a solution of trichloroacetamide (0.532 g, 3.27 mmol). The reaction mixture was stirred at room temperature for 15 min. The reaction mixture poured into ice water (30 mL), and then, extracted by ethyl acetate. The organic layer was washed with brine, dried over Na₂SO₄ and concentrated under reduced pressure, and purified by silica gel column chromatography (hexane:ethyl acetate = 7:3) to give (2-chloroethyl)benzene (0.220 g, 97% yield) as a colorless liquid.

The reaction mixture was monitored by TLC (hexane:ethyl acetate = 4:1, Rf = 0.7).

¹H NMR (400 MHz, CDCl₃); δ 7.36-7.21 (m, 5H), 3.72 (t, 2H, J = 11.2 Hz), 3.07 (t, 2H, J = 11.2 Hz).

¹³C NMR (101 MHz, CDCl₃); δ 138.1, 128.8, 128.6, 126.9, 44.9, 33.2.

• An efficient method for chlorination of alcohols using PPh₃/Cl₃CCONH₂
• W. Pluempanupat, W. Chavasiri, Tetrahedron Lett. 2006, 47, 6821.