N-bromobutanimide → 5-(Bromomethyl)benzo[b]thiophene

HRID 2304901Notes

Reaction equation

HRID 2304901 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]2[S:6][CH:7]=[CH:8][C:4]=2[CH:3]=1.[Br:11]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:11][CH2:1][C:2]1[CH:10]=[CH:9][C:5]2[S:6][CH:7]=[CH:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 843465-Methylbenzo(b)thiophene

Product 1

HCID 111604985-(Bromomethyl)benzo[b]thiopheneYield 87.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-methylbenzo[b]thiophene (5.0 g, 33.7 mmol), N-bromosuccinimide (5.7 g, 32.0 mmol) and dibenzoylperoxide (0.25 g, 1.01 mmol) in tetrachloromethane was heated to reflux for 2 hours. It was cooled to room temperature and left for 16 hours. The solid was filtered off. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (300 g), using ethyl acetate/heptane (1:10) as eluent, to give 6.37 g (83%) of 5-bromomethylbenzo[b]thiophene.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. filtrationThe solid was filtered off
  4. customThe solvent was removed in vacuo
  5. customThe crude product was purified by flash chromatography on silica (300 g)

Sources & evidence

ORD record
ord-36283f25996d469daa4f1fa122c7fe0e
Source dataset
uspto-grants-2002_08
Patent number
US06437147B1

Reaction notes

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