Reaktion #569158

Reaktionsgleichung

5-bromo-3-methylbenzothiophene

N-bromosuccinimide

→

desired compound

Ausbeute 74.0%

5-bromo-3-(bromomethyl)benzothiophene

Ausbeute 74.0%

Lösungsmittel

carbon tetrachloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 3 hours
2. 2
   Filtrationfiltered
3. 3
   Einengenthe filtrate concentrated under reduced pressure
4. 4
   Wascheneluting with hexane
5. 5
   workup.ADDITIONFractions containing the desired compound
6. 6
   Einengenconcentrated under reduced pressure

Vorschrift

A solution of 4.30 gm (18.9 mMol) 5-bromo-3-methylbenzothiophene, 0.25 gm (1.03 mMol) benzoylperoxide, and 3.37 gm (18.9 mMol) N-bromosuccinimide in 50 mL carbon tetrachloride was heated at reflux for 3 hours. The reaction mixture was cooled to room temperature, filtered and the filtrate concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, eluting with hexane. Fractions containing the desired compound were combined and concentrated under reduced pressure to provide 4.28 gm (74%) of the desired compound.

Quelle