Benzoyl Peroxide → 5-(Bromomethyl)benzo[b]thiophene

HRID 546250Notes

Reaction equation

HRID 546250 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.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[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 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 843465-Methylbenzo(b)thiophene

Product 1

HCID 111604985-(Bromomethyl)benzo[b]thiopheneYield 94.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
76 °C

Procedure

In a flask was placed 5-methyl-benzo[b]thiophene (3.64 g, 24.56 mmol) and carbon tetrachloride (75 mL). To the reaction mixture was then added N-bromosuccinimide (5.68 g, 31.92 mmol) and benzoyl peroxide (892 mg, 3.68 mmol) and it was the final solution was then heated at 76° C. for 6 h. After this time the reaction mixture was cooled to 0° C. in an ice bath and the solids were filtered off and the filterate was concentrated in vacuo and purified on an AnaLogix Intelliflash system (120 g column, 3% ethyl acetate/hexanes) to afford 5-bromomethyl-benzo[b]thiophene (5.27 g, 94%) as a yellow solid.

Workup

  1. customIn a flask was placed
  2. temperatureAfter this time the reaction mixture was cooled to 0° C. in an ice bath
  3. filtrationthe solids were filtered off
  4. concentrationthe filterate was concentrated in vacuo
  5. custompurified on an AnaLogix Intelliflash system (120 g column, 3% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d7512f82aa524c42b66bc69de1b40e53
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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