Bromine → 3'-Bromo-4'-(bromomethyl)biphenyl-2-carbonitrile

HRID 1609200Notes

Reaction equation

HRID 1609200 reaction equation
[Br:1]Br.[Br:3][C:4]1[CH:5]=[C:6]([C:11]2[C:12]([C:17]#[N:18])=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:7]=[CH:8][C:9]=1[CH3:10]>ClCC(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:3][C:4]1[CH:5]=[C:6]([C:11]2[C:12]([C:17]#[N:18])=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:7]=[CH:8][C:9]=1[CH2:10][Br:1]

Participants

5

Reactant 2

HCID 24408BromineHCID 218403383'-Bromo-4'-methyl-1,1'-biphenyl-2-carbonitrile

Product 1

HCID 218403713'-Bromo-4'-(bromomethyl)biphenyl-2-carbonitrileYield 33,370.602%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 124181,1,1,2-TetrachloroethaneSolvent2×

Procedure

5.6 g (0.035 mmol) of bromine, dissolved in 20 ml of tetrachloroethane, are added dropwise at 100°-110° with UV irradiation to a solution of 8.9 g (0.033 mol) of 3'-bromo-4' -methyl-1,1'-biphenyl-2-carbonitrile in 900 ml of tetrachloroethane after addition of 0.1 g of benzoyl peroxide. After 30 minutes, the reaction mixture is cooled and evaporated in vacuo. The crystalline residue is recrystallized from ethyl acetate and gives 4.1 g of the title compound of m.p. 152°-153°.

Workup

  1. temperaturethe reaction mixture is cooled
  2. customevaporated in vacuo
  3. customThe crystalline residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-67a080bb954e41eba06ee1dcb70aa945
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

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