Benzoyl Peroxide → 4'-(Bromomethyl)-2-cyanobiphenyl

HRID 274245Notes

Reaction equation

HRID 274245 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)#[N:2].[Br:16]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClCCCl>[Br:16][CH2:15][C:12]1[CH:11]=[CH:10][C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:1]#[N:2])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 1455122-Cyano-4'-methylbiphenyl

Product 1

HCID 15019124'-(Bromomethyl)-2-cyanobiphenyl

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

The 467.3 g of 2-cyano-4'-methylbiphenyl prepared above are dissolved in 4.7l of 1,2-dichloroethane in the presence of 467.3 g of N-bromosuccinimide and 9.3 g of benzoyl peroxide. The mixture is heated very gradually so as to have good control over the exothermic effect. It is subsequently refluxed for 4 h, cooled to 50° C. and then washed 3 times with hot water and dried and the organic phase is concentrated to give cream-colored crystals.

Workup

  1. temperatureThe mixture is heated very gradually so as
  2. temperatureIt is subsequently refluxed for 4 h
  3. washwashed 3 times with hot water
  4. customdried
  5. concentrationthe organic phase is concentrated
  6. customto give cream-colored crystals

Sources & evidence

ORD record
ord-32aa504c108a4e5aa8d92ff790d150bf
Source dataset
uspto-grants-1995_02
Patent number
US05389632

Reaction notes

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