Benzoyl Peroxide → 3-(4-(Bromomethyl)phenyl)thiophene

HRID 1957019Notes

Reaction equation

HRID 1957019 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=2)=[CH:2]1.[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][Br:13])=[CH:8][CH:7]=2)=[CH:2]1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 41303473-(4-Methylphenyl)thiophene

Product 1

HCID 137735383-(4-(Bromomethyl)phenyl)thiophene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 4-(3-thienyl)toluene (3.56 g, 20.5 mmol) in carbon tetrachloride (100 ml) is added N-bromosuccinimide (3.64 g, 20.5 mol) and benzoyl peroxide (80 mg, 3.3 mmol). The reaction mixture is heated at reflux for 24 hrs. and concentrated in vacuo. The reaction mixture is recrystallized from ethanol to afford 4-(3-thienyl)benzyl bromide.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 24 hrs
  3. concentrationand concentrated in vacuo
  4. customThe reaction mixture is recrystallized from ethanol

Sources & evidence

ORD record
ord-ef8bed6f4a65437fb5f42700a13c9323
Source dataset
uspto-grants-1998_07
Patent number
US05780498

Reaction notes

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