N-bromobutanimide → 4-Acetoxy-2-chlorobenzylbromide

To a solution of 4-acetoxy-2-chlorotoluene (13.4 g) in carbon tetrachloride (134 ml) were added N-bromosuccinimide (12.9 g) and 2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile) (1.12 g), and the mixture was refluxed under heating for 2.5 hr. The reaction mixture was concentrated to dryness under reduced pressure. To the residue was added hexane (270 ml) and the mixture was stirred at room temperature for 10 min. The insoluble matter was filtered off and washed with hexane. The filtrate and washing were combined and washed 3 times with saturated aqueous sodium hydrogen carbonate solution and once with saturated brine. The organic layer was dried over magnesium sulfate and concentrated to dryness under reduced pressure. The residue was crystallized from hexane to give 4-acetoxy-2-chlorobenzylbromide as colorless crystals (11.3 g).

1. temperaturethe mixture was refluxed
2. temperatureunder heating for 2.5 hr
3. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
4. additionTo the residue was added hexane (270 ml)
5. filtrationThe insoluble matter was filtered off
6. washwashed with hexane
7. washThe filtrate and washing
8. washwashed 3 times with saturated aqueous sodium hydrogen carbonate solution
9. dry with materialThe organic layer was dried over magnesium sulfate
10. concentrationconcentrated to dryness under reduced pressure
11. customThe residue was crystallized from hexane

ORDレコード

ord-643eb67536bd4463b2be2b975b623111

出典データセット

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06573274B1