Benzoyl Peroxide → 1-(Bromomethyl)-2-chloro-3-methylbenzene

HRID 1042347

Reaction equation

HRID 1042347 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].C1C(=O)N([Br:17])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 328851-Chloro-2,6-dimethylbenzeneHCID 67184N-bromobutanimide

Product 1

HCID 153644661-(Bromomethyl)-2-chloro-3-methylbenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 2-chloro-m-xylene (5.00 g, 35.60 mmol), NBS (5.70 g, 32.03 mmol), and a catalytic amount of benzoyl peroxide (100 mg) in CCl4 was refluxed for 1 hour. After cooling to room temperature the resulting mixture was filtered and the filtrate was distilled off. Purification by column chromatography using pentane as the eluant followed by distillation afforded the title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3.) δ 2.39 (s, 3H), 4.61 (s, 2H), 7.08-7.23 (m, 2H), 7.25-7.30 (m, 1H).

Workup

  1. filtrationwas filtered
  2. distillationthe filtrate was distilled off
  3. customPurification by column chromatography
  4. distillationfollowed by distillation

Sources & evidence

ORD record
ord-e569125c88214a4ab8e24fa7f3a77c0e
Source dataset
uspto-grants-2013_10
Patent number
US08557853B2

Linked notes

Loading…