Benzoyl Peroxide → 3-[2-(Bromomethyl)phenyl]thiophene

HRID 745529Notes

Reaction equation

HRID 745529 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH3:12])=[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][CH:9]=[CH:8][C:7]=2[CH2:12][Br:13])=[CH:2]1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 41303453-(2-Methylphenyl)thiophene

Product 1

HCID 135529933-[2-(Bromomethyl)phenyl]thiophene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of Compound 2a (7.23 mmol) in carbon tetrachloride (150 mL) was added N-bromosuccinimide (7.5 mmol) and benzoyl peroxide (0.1 g). The solution was heated at reflux and irradiated with 250 watt sunlamp for 2 hours. The cooled reaction mixture was filtered through a pad of silica gel and the silica gel washed with diethyl ether (3×75 mL). The solvent was removed in vacuo and the residue fractionated to afford Compound 2b as a clear oil (b.p. 100°-103° C./0.1 mm).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux
  3. customirradiated with 250 watt sunlamp for 2 hours
  4. customThe cooled reaction mixture
  5. filtrationwas filtered through a pad of silica gel
  6. washthe silica gel washed with diethyl ether (3×75 mL)
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-68c5656836c04b0db1ae2c8128d91679
Source dataset
uspto-grants-1986_07
Patent number
US04599341

Reaction notes

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