N-bromobutanimide → 2-Chloro-4-(tert-butyl)benzyl bromide

HRID 1927395Notes

Reaction equation

HRID 1927395 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([Cl:20])[CH:14]=1)([CH3:12])([CH3:11])[CH3:10]>ClC(Cl)(Cl)Cl>[Cl:20][C:15]1[CH:14]=[C:13]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:18]=[CH:17][C:16]=1[CH2:19][Br:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 5243374-Tert-butyl-2-chloro-1-methylbenzene

Product 1

HCID 578313342-Chloro-4-(tert-butyl)benzyl bromide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

1.75 g (9.85 mmol) of N-bromosuccinimide and 10.8 mg (0.006 mmol) of 2,2′-azobis-2-methylpropanenitrile are added to a solution of 2 g (10.95 mmol) of 4-tert-butyl-2-chloro-1-methylbenzene in 10 ml of tetrachloromethane, and the mixtures is stirred under reflux for 4 hours. After cooling, the mixture is concentrated. The residue is purified by flash chromatography on silica gel (mobile phase, cyclohexane). 2.1 g (38% of theory) of the title compound are obtained with a purity of 52%.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated
  4. customThe residue is purified by flash chromatography on silica gel (mobile phase, cyclohexane)

Sources & evidence

ORD record
ord-f6fc1aec95ad4babac6bd6e794a2ad3b
Source dataset
uspto-grants-2012_05
Patent number
US08183271B2

Reaction notes

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