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

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

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.