Benzoyl Peroxide → (2-Bromomethyl-4-chloro-6-methyl-phenoxy)-acetonitrile

HRID 988283Notes

Reaction equation

HRID 988283 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:5]([O:6][CH2:7][C:8]#[N:9])=[C:4]([CH3:13])[CH:3]=1.[Br:14]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:13][C:4]1[CH:3]=[C:2]([Cl:1])[CH:11]=[C:10]([CH3:12])[C:5]=1[O:6][CH2:7][C:8]#[N:9]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 222413682-(4-Chloro-2,6-dimethylphenoxy)acetonitrile

Product 1

HCID 22241394(2-Bromomethyl-4-chloro-6-methyl-phenoxy)-acetonitrile

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

(4-Chloro-2,6-dimethyl-phenoxy)-acetonitrile (700 mg, 3.6 mmol), N-bromosuccinimide (510 mg, 2.9 mmol) and benzoyl peroxide (72 mg, 0.29 mmol) are heated at reflux in carbon tetrachloride (10 mL) for 16 h. The reaction is cooled, filtered and the filtrate is concentrated and purified by column chromatograpy (silica, 5% ethyl acetate in hexanes) to provide the title compound. MS (EI) 273, 275 (M)+, Br pattern.

Workup

  1. temperatureThe reaction is cooled
  2. filtrationfiltered
  3. concentrationthe filtrate is concentrated
  4. custompurified by column chromatograpy (silica, 5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-df8b0d7e739845e2b481a2cee720f4a3
Source dataset
uspto-grants-2003_10
Patent number
US06635655B1

Reaction notes

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