Benzoyl Peroxide → 2-(Bromomethyl)-5-chloro-1-benzothiophene

HRID 2187637Notes

Reaction equation

HRID 2187637 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH3:10])=[CH:7][C:6]=2[CH:11]=1.C1C(=O)N([Br:19])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:10][C:8]1[S:9][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:11][C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 2747689HCID 2747689, compound

Product 1

HCID 136426062-(Bromomethyl)-5-chloro-1-benzothiopheneYield 97.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 2.73 g (14.95 mmol) 5-chloro-2-methylbenzothiophene and 2.67 g (15.0 mmol) NBS in 100 ml carbon tetrachloride was heated to 70° C. and a catalytic amount of dibenzoyl peroxide was added. After 30 min reflux solids were removed by filtration. The solvent was removed in vacuo and the residue was suspended in 100 ml hot hexane and filtered. The filtrate was evaporated to dryness to give 3.8 g (97%) of the title compound as a colorless solid.

Workup

  1. temperatureAfter 30 min reflux solids
  2. customwere removed by filtration
  3. customThe solvent was removed in vacuo
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-ad5f07453d094c149062c1a63b92adea
Source dataset
uspto-grants-2002_06
Patent number
US06410562B1

Reaction notes

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