Thionyl Chloride → 3-((3,3,3-Trifluoropropyl)thio)propanoyl chloride

Temperature

36 °C

A dry 5 L round bottom flask equipped with magnetic stirrer, nitrogen inlet, reflux condenser, and thermometer, was charged with 3-((3,3,3-trifluoropropyl)thio)propanoic acid (188 g, 883 mmol) in dichloromethane (3 L). Thionyl chloride (525 g, 321 mL, 4.42 mol) was then added dropwise over 50 minutes. The reaction mixture was heated to reflux (about 36° C.) for two hours, then cooled to room temperature. Concentration under vacuum on a rotary evaporator, followed by distillation (40 Torr, product collected from 123-127° C.) gave the title compound as a clear colorless liquid (177.3 g, 86%): 1H NMR (400 MHz, CDCl3) δ 3.20 (t, J=7.1 Hz, 2H), 2.86 (t, J=7.1 Hz, 2H), 2.78-2.67 (m, 2H), 2.48-2.31 (m, 2H); 19F NMR (376 MHz, CDCl3) δ −66.42, −66.43, −66.44, −66.44.

1. customA dry 5 L round bottom flask equipped with magnetic stirrer, nitrogen inlet
2. temperaturereflux condenser
3. temperatureThe reaction mixture was heated
4. temperaturecooled to room temperature
5. concentrationConcentration under vacuum
6. customon a rotary evaporator
7. distillationfollowed by distillation (40 Torr, product collected from 123-127° C.)

ORD record

ord-ad785750ff4e47daa3a7d7a0d8aaf59b

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108946B2