N-bromobutanimide → 3-Bromomethyl-4-chloro-5-methyl-benzonitrile

HRID 2194790Notes

Reaction equation

HRID 2194790 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:11].[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:12][CH2:10][C:9]1[CH:8]=[C:5]([CH:4]=[C:3]([CH3:11])[C:2]=1[Cl:1])[C:6]#[N:7]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 575173244-Chloro-3,5-dimethyl-benzonitrile

Product 1

HCID 670504963-Bromomethyl-4-chloro-5-methyl-benzonitrileYield 66.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-chloro-3,5-dimethyl-benzonitrile (1.011 g, 6.10 mmol), N-bromosuccinimide (1.087 g, 6.10 mmol) and benzoyl peroxide (0.074 g, 0.305 mmol) in carbon tetrachloride (30 mL) was heated to reflux for 4 hr. The reaction mixture was cooled to room temperature and filtered. The filtrate was purified by flash column chromatography (silica gel, 0 to 30% ethyl acetate/hexane) to give 3-bromomethyl-4-chloro-5-methyl-benzonitrile as an impure white solid (0.9938 g, 66%), which was used in the next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hr
  3. filtrationfiltered
  4. customThe filtrate was purified by flash column chromatography (silica gel, 0 to 30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4042390a95ca41c7b511f5f04097d286
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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