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

HRID 2266619Notes

Reaction equation

HRID 2266619 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[C:5]#[N:6].[Br:11]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 888943-Chloro-p-toluonitrile

Product 1

HCID 130420934-(Bromomethyl)-3-chlorobenzonitrile

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-chloro-4-methylbenzonitrile (4.8 g), N-bromosuccinimide (5.5 g), dibenzoyl peroxide (0.43 g) and carbon tetrachloride (30 mL) was heated a reflux for 2 hours. The mixture was cooled to room temperature, filtered and washed with dichloromethane. The filtrated was washed with water, dried over sodium sulfate and the solvent removed under reduced pressure. Purification of the residue by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (1:0 to 19:1 by volume) gave title compound, 4.1 g.

Workup

  1. temperaturewas heated
  2. temperaturea reflux for 2 hours
  3. filtrationfiltered
  4. washwashed with dichloromethane
  5. washThe filtrated was washed with water
  6. dry with materialdried over sodium sulfate
  7. customthe solvent removed under reduced pressure
  8. customPurification of the residue by column chromatography on silica gel
  9. washeluting with a mixture of cyclohexane and ethyl acetate (1:0 to 19:1 by volume)

Sources & evidence

ORD record
ord-67805ab1faef48ec832b36c6eb8f4766
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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