Ethanol → Ethyl 4-bromobutyrate

A solution of 4-bromobutanoic acid (25.0 g, 150 mmol), DMF (5 drops) and oxalyl chloride (17.0 mL, 195.0 mmol) in dichloromethane (250 mL) was stirred at room temperature for 5 hr. The reaction mixture was concentrated under reduced pressure, dichloromethane (200 mL) and ethanol (9.0 mL, 170 mmol) were added to the residue, and the mixture was stirred at room temperature for 15 hr. The reaction mixture was washed with saturated aqueous sodium hydrogencarbonate and saturated brine, and the organic layer was dried over sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (0-5% ethyl acetate/hexane) to give ethyl 4-bromobutanoate as a colorless oil (24.5 g, 84%).

1. additionwere added to the residue
2. washThe reaction mixture was washed with saturated aqueous sodium hydrogencarbonate and saturated brine
3. dry with materialthe organic layer was dried over sodium sulfate
4. concentrationconcentrated
5. customThe residue was purified by silica gel column chromatography (0-5% ethyl acetate/hexane)

ORD record

ord-0709879ff8b64625939c4164d962e04e

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07915267B2