1-Bromo-2-Chloroethane → 3-(2-Chloroethoxy)benzonitrile

Temperature

90 °C

A suspension of 3-hydroxybenzonitrile (5.00 g, 42.0 mmol), 1-bromo-2-chloroethane (9.00 g, 62.8 mmol) and potassium hydroxide (2.5 g, 44.6 mmol) in ethanol (100 mL) was stirred at 90° C. for 24 hr. The reaction mixture was concentrated under reduced pressure, and the residue was extracted with diethyl ether and water. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The obtained oil was purified by silica gel column chromatography (2%-50% ethyl acetate/hexane) to give the title compound as a colorless oil (1.39 g, 18%).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. extractionthe residue was extracted with diethyl ether and water
3. washThe organic layer was washed with saturated brine
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated
6. customThe obtained oil was purified by silica gel column chromatography (2%-50% ethyl acetate/hexane)

ORD record

ord-95d6f0d0116440ea9754a925f1b3443b

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07915267B2