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

HRID 2117236Notes

Reaction equation

HRID 2117236 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 (ES) 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-abb79408b8df47af8cdc7e391e3f9f72
Source dataset
uspto-grants-2008_10
Patent number
USRE040558E1

Reaction notes

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