Benzoyl Peroxide → 2-(2-Bromomethylphenyl)-2-difluoromethoxyimino-acetonitrile

HRID 726859Notes

Reaction equation

HRID 726859 reaction equation
[F:1][CH:2]([F:15])[O:3][N:4]=[C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14])[C:6]#[N:7].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:34]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:34][CH2:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:5](=[N:4][O:3][CH:2]([F:15])[F:1])[C:6]#[N:7]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 57050284alpha-Difluoromethoxyimino-o-tolylacetonitrile

Product 1

HCID 545412962-(2-Bromomethylphenyl)-2-difluoromethoxyimino-acetonitrile

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 8.0 g of α-difluoromethoxyimino-o-tolylacetonitrile and 0.07 g of dibenzoyl peroxide in 50 ml of carbon tetrachloride is heated to reflux. With radiation from a lamp, 6.77 g of N-bromosuccinimide are added thereto in several small portions and the mixture is left to react for 0.5 hour. The reaction mixture is cooled to room temperature, the succinimide is filtered off and the residue is concentrated by evaporation. Chromatography on silica gel with hexane/ethyl acetate (15:1) yields pure 2-(2-bromomethylphenyl)-2-difluoromethoxyimino-acetonitrile in the form of a pale yellow oil.

Workup

  1. waitin several small portions and the mixture is left
  2. customto react for 0.5 hour
  3. filtrationthe succinimide is filtered off
  4. concentrationthe residue is concentrated by evaporation

Sources & evidence

ORD record
ord-88301543e6554e70a4fe4e70b4bf86b8
Source dataset
uspto-grants-1998_01
Patent number
US05710314

Reaction notes

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