N-bromobutanimide → 5-Bromo-3-(bromomethyl)-1-benzothiophene

HRID 481976Notes

Reaction equation

HRID 481976 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[C:7]([CH3:10])[C:6]=2[CH:11]=1.[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[C:7]([CH2:10][Br:12])[C:6]=2[CH:11]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 141757645-Bromo-3-methyl-1-benzothiophene

Product 1

HCID 217904115-Bromo-3-(bromomethyl)-1-benzothiopheneYield 74%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

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.

Workup

  1. temperatureat reflux for 3 hours
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. washeluting with hexane
  5. additionFractions containing the desired compound
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-776cab91e17c4389b641455b46db93a8
Source dataset
uspto-grants-1998_08
Patent number
US05792763

Reaction notes

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