1-Bromo-3-chloropropane → 3-(3-Chloropropoxy)benzonitrile

A suspension of 1-bromo-3-chloropropane (13.9 g, 88.1 mmol) and 60% sodium hydride (oil dispersion, 3.02 g, 126 mmol) in ethanol (50 mL) was stirred at room temperature for 30 min. 3-Hydroxybenzonitrile (10.0 g, 83.9 mmol) was added to the reaction mixture at 0° C., and the mixture was stirred at 60° C. for 15 hr. The reaction mixture was concentrated under reduced pressure, and the residue was extracted with ethyl acetate 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 (5%-15% ethyl acetate/hexane) to give the title compound as a colorless oil (14.2 g, 86%).

1. stirringthe mixture was stirred at 60° C. for 15 hr
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. extractionthe residue was extracted with ethyl acetate and water
4. washThe organic layer was washed with saturated brine
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated
7. customThe obtained oil was purified by silica gel column chromatography (5%-15% ethyl acetate/hexane)

ORD record

ord-960b90b491554959a328a1426f7827ca

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07915267B2