Thionyl Chloride → 2-(4-Chlorophenyl)ethyl chloride

Temperature

67.5 °C

Into a 250-mL round-bottom flask equipped with magnetic stirring, a thermocouple, a condenser, and a nitrogen bubbler vented to caustic scrubber, was charged 2-(4-chlorophenyl)ethanol (25.011 g, 160 mmol), N,N-dimethylacetamide (0.748 mL, 7.99 mmol), and toluene (73 mL). The mixture was heated to 65 to 70° C. and then thionyl chloride (12.24 mL, 168 mmol) was added over 1 h. The reaction was stirred at 60 to 68° C. for 2 h to give a dark-brown solution. This solution was cooled to 45° C., washed with water (2×27 mL) and saturated aqueous sodium bicarbonate (3×27 mL) at 40 to 45° C., and then cooled room temperature and allowed to stir overnight.

1. customInto a 250-mL round-bottom flask equipped with magnetic stirring
2. customto give a dark-brown solution
3. temperatureThis solution was cooled to 45° C.
4. washwashed with water (2×27 mL) and saturated aqueous sodium bicarbonate (3×27 mL) at 40 to 45° C.
5. temperaturecooled room temperature
6. stirringto stir overnight

ORD record

ord-77353034c6974a1e80f876b04a65d920

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952197B2