Benzoyl Peroxide → 4-(Bromomethyl)-3-nitrobenzonitrile

HRID 1296771Notes

Reaction equation

HRID 1296771 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.ClCCl>[Br:13][CH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 5893334-Methyl-3-nitrobenzonitrile

Product 1

HCID 219055094-(Bromomethyl)-3-nitrobenzonitrileYield 45%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-methyl-3-nitro-benzonitrile (3.0 g, 18.5 mmol), N-bromosuccinimide (4.12 g), and benzoyl peroxide (0.224 g) in carbon tetrachloride was refluxed overnight. The reaction mixture was diluted with dichloromethane and washed with sodium bicarbonate solution and brine, dried, and concentrated. The residue was purified by silica gel chromatography in 10% ethyl acetate hexanes to give compound 65a (2.0 g, 45%).

Workup

  1. washwashed with sodium bicarbonate solution and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography in 10% ethyl acetate hexanes

Sources & evidence

ORD record
ord-4e77aa5919fc4b03a551016cb6e70dea
Source dataset
uspto-grants-2007_07
Patent number
US07247654B2

Reaction notes

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