N-bromobutanimide → 2-Bromo-1-(bromomethyl)-4-fluorobenzene

Combine 2-bromo-4-fluoro-1-methyl-benzene (15 g, 79.3 mmol), N-bromosuccinimide (18.08 g, 101.6 mmol), and 2,2-azobisisobutyronitrile (3.9 g, 23.8 mmol) in carbon tetrachloride (150 mL) in a round bottom flask fitted with a reflux condensor. Heat the mixture at reflux for 21 h. Cool the mixture and remove the solvent under reduced pressure. Suspend the crude mixture in DCM and wash with water. Wash the organics with aqueous saturated sodium chloride and dry over sodium sulfate. Filter and remove the solvent under reduced pressure to obtain the crude product. Purify by column chromatography (1% ethyl acetate in hexane→10% ethyl acetate in hexanes) to give the title compound as an oily white solid (18.5 g, 87%). GCMS m/z 268 [M]+.

1. temperatureHeat the mixture
2. temperatureat reflux for 21 h
3. temperatureCool the mixture
4. customremove the solvent under reduced pressure
5. washwash with water
6. washWash the organics with aqueous saturated sodium chloride
7. dry with materialdry over sodium sulfate
8. filtrationFilter
9. customremove the solvent under reduced pressure
10. customto obtain the crude product
11. customPurify by column chromatography (1% ethyl acetate in hexane→10% ethyl acetate in hexanes)

ORDレコード

ord-780b41ee347a492496f85533b11dceed

出典データセット

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08063035B2