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

HRID 576944

Reaction equation

HRID 576944 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:11].[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 775912-Chloro-3-nitrotoluene

Product 1

HCID 183630451-(Bromomethyl)-2-chloro-3-nitrobenzeneYield 47.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-chloro-1-methyl-3-nitrobenzene (1 g, 5.8 mmol) was dissolved in CCl4 (10 mL), then N-bromosuccinimide (2.28 g, 12.8 mmol) and benzoyl peroxide (846 mg, 3.5 mmol) were added. The mixture was stirred overnight at reflux. The solid was removed by filtration, and the filtrate was washed with water and dried over sodium sulfate. After evaporation of the solvent, the residue was dissolved in DCM and purified on silica gel using 30% hexane/AcOEt to afford 1-(bromomethyl)-2-chloro-3-nitrobenzene (686 mg, 47% yield); 1H NMR (400 MHz, CDCl3): δ 4.64 (s, 2H), 7.42 (t, J=7.9 Hz, 1H), 7.67 (dd, J=1.6 Hz, J=7.9 Hz, 1H), 7.75 (dd, J=1.6 Hz, J=7.9 Hz, 1H).

Workup

  1. temperatureat reflux
  2. customThe solid was removed by filtration
  3. washthe filtrate was washed with water
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation of the solvent
  6. dissolutionthe residue was dissolved in DCM
  7. custompurified on silica gel using 30% hexane/AcOEt

Sources & evidence

ORD record
ord-8ed8841e752744188bb8075fc0278371
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Linked notes

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