Benzoyl Peroxide → 3-Bromomethyl-5-chloro-2-phenylbenzo[b]thiophene

HRID 985756Notes

Reaction equation

HRID 985756 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:7]([CH3:16])[C:6]=2[CH:17]=1.[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:16][C:7]1[C:6]2[CH:17]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[S:9][C:8]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 8219825-Chloro-3-methyl-2-phenyl-1-benzothiophene

Product 1

HCID 219167743-Bromomethyl-5-chloro-2-phenylbenzo[b]thiophene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

In a 100 ml round-bottomed flask, 1 eq. of the compound obtained in Step B is dissolved in 20 ml of CCl4. 1 eq. of N-bromosuccinimide and 0.04 eq. of benzoyl peroxide are then added, and the mixture is irradiated by means of a halogen lamp and maintained at reflux for 4 hours. At the end of the reaction, the insoluble material is filtered off, and the carbon tetrachloride is evaporated off. The residue obtained is purified by chromatography on a silica gel column.

Workup

  1. customthe mixture is irradiated by means of a halogen lamp
  2. temperaturemaintained
  3. temperatureat reflux for 4 hours
  4. customAt the end of the reaction
  5. filtrationthe insoluble material is filtered off
  6. customthe carbon tetrachloride is evaporated off
  7. customThe residue obtained
  8. customis purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-2e4ca7c5a58e4dc3b50567ecb43d6a3d
Source dataset
uspto-grants-2005_03
Patent number
US06872851B1

Reaction notes

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