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

HRID 892172Notes

Reaction equation

HRID 892172 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, example 42), 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-c2b5e3e6e2964249bf7e7f4a58340f60
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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