3,3'-Dimethylbiphenyl → 3-(Bromomethyl)-3'-methyl-1,1'-biphenyl

HRID 1995117Notes

Reaction equation

HRID 1995117 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:15][CH2:14][C:10]1[CH:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 119313,3'-DimethylbiphenylHCID 67184N-bromobutanimide

Product 1

HCID 202706053-(Bromomethyl)-3'-methyl-1,1'-biphenylYield 15.7%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

3-Bromomethyl-3'-methyl[1,1'-biphenyl] was prepared by treating 3,3'-dimethyl[1,1'-biphenyl] (20.0 g, 0.11 mole) with N-bromosuccinimide (18.9 g, 0.11 mole) in the presence of 0.1 g of benzoyl peroxide in 130 ml of carbon tetrachloride. Irradiation of the reaction mixture with white light afforded 3-bromomethyl-3'-methyl-[1,1'-biphenyl] (4.5 g). The nmr and the ir spectra were consistent with the proposed structure.

Workup

  1. custom3-Bromomethyl-3'-methyl[1,1'-biphenyl] was prepared
  2. customIrradiation of the reaction mixture with white light

Sources & evidence

ORD record
ord-d3075dc2bce14dac91e15b2746f79a2d
Source dataset
uspto-grants-1983_09
Patent number
US04402973

Reaction notes

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