Benzoyl Peroxide → 4-(4-Bromomethyl-3-chloro-phenoxy)-2-chloro-benzonitrile

HRID 2096845Notes

Reaction equation

HRID 2096845 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([Cl:18])[CH:12]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Br:19]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][C:8]2[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([Cl:1])[CH:9]=2)=[CH:12][C:13]=1[Cl:18]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 666970942-Chloro-4-(3-chloro-4-methyl-phenoxy)-benzonitrile

Product 1

HCID 666971204-(4-Bromomethyl-3-chloro-phenoxy)-2-chloro-benzonitrileYield 17.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of 2-chloro-4-(3-chloro-4-methyl-phenoxy)-benzonitrile (14.41 g) in CCl4 (100 ml) under argon were added N-bromosuccinimide (9.5 g) and dibenzoylperoxide (1.38 g). The mixture was heated to reflux for 2.5 h. After cooling to room temperature, the mixture was filtered. The filter cake was washed with cyclohexane. The combined filtrate was concentrated to dryness to give the crude product (19.75 g) as a light orange solid. Part of the product was purified by repeated chromatography (SiO2, cyclohexane/ethyl acetate 1:0=>4:1) to give the title compound as an off-white solid (3.27 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2.5 h
  3. filtrationthe mixture was filtered
  4. washThe filter cake was washed with cyclohexane
  5. concentrationThe combined filtrate was concentrated to dryness
  6. customto give the crude product (19.75 g) as a light orange solid
  7. customPart of the product was purified by repeated chromatography (SiO2, cyclohexane/ethyl acetate 1:0=>4:1)

Sources & evidence

ORD record
ord-4a8454ce0b4342d2b61e2430bc567876
Source dataset
uspto-grants-2013_05
Patent number
US08450313B2

Reaction notes

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