Benzoyl Peroxide → 3-(Bromomethyl)biphenyl

HRID 1957003

Reaction equation

HRID 1957003 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Br:14]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:8]1([C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=2)[CH2:1][Br:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 125643-MethylbiphenylHCID 67184N-bromobutanimide

Product 1

HCID 38644053-(Bromomethyl)biphenyl

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-methylbiphenyl (5.23 g, 31.1 mmol), N-bromosuccinimide (5.56 g, 31.2 mmol), benzoyl peroxide (135 mg, 0.56 mmol), and carbon tetrachloride (150 ml) is refluxed for 17 h. The mixture is concentrated in vacuo and the residue is purified by flash column chromatography (hexane) to give 3-phenylbenzyl bromide.

Workup

  1. temperatureis refluxed for 17 h
  2. concentrationThe mixture is concentrated in vacuo
  3. customthe residue is purified by flash column chromatography (hexane)

Sources & evidence

ORD record
ord-e6b235cc9e144fd1a618c058180307e5
Source dataset
uspto-grants-1998_07
Patent number
US05780498

Linked notes

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