Benzoyl Peroxide → 4-Bromo-2-(bromomethyl)benzonitrile

HRID 2220223Notes

Reaction equation

HRID 2220223 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=1.[Br:11]NC(=O)CCC(N)=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH2:10][Br:11])[CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 1442674-Bromo-2-methylbenzonitrileHCID 9834204N-Bromosuccinamide

Product 1

HCID 251406084-Bromo-2-(bromomethyl)benzonitrileYield 102.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred mixture of 4-Bromo-2-methyl-benzonitrile (5.00 g, 25.5 mmol) in CCl4 (40 mL) under argon was added N-bromosuccinamide (5.00 g, 28.1 mmol) and a catalytic amount of benzoyl peroxide. This mixture was heated at 85° C. for 2 days and cooled to room temperature. The precipitate was filtered off and the cake was rinsed with CCl4 (2×10 mL). The filtrate was concentrated in vacuo to give 7.2 g crude 4-Bromo-2-bromomethyl-benzonitrile (quantitative yield) which was used without further purification.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe precipitate was filtered off
  3. washthe cake was rinsed with CCl4 (2×10 mL)
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f5b83e452c964f2b90ffde53367cf9bf
Source dataset
uspto-grants-2008_08
Patent number
US07417040B2

Reaction notes

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