N-bromobutanimide → 3-Bromo-2-(bromomethyl)benzonitrile

HRID 1492757Notes

Reaction equation

HRID 1492757 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[Br:9][C:10]1[C:11]([CH3:18])=[C:12]([CH:15]=[CH:16][CH:17]=1)[C:13]#[N:14]>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:9][C:10]1[C:11]([CH2:18][Br:8])=[C:12]([CH:15]=[CH:16][CH:17]=1)[C:13]#[N:14]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 234335373-Bromo-2-methylbenzonitrile

Product 1

HCID 189509413-Bromo-2-(bromomethyl)benzonitrileYield 86.9%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of NBS (3.45 g), dibenzoyl peroxide (100 mg) and 3-bromo-2-methylbenzonitrile (3.47 g) in carbon tetrachloride (40 ml) was heated at reflux under nitrogen for 48 h. The mixture was then cooled to room temperature, filtered and concentrated in vacuo to give a pale yellow solid. Chromatography eluting with dichloromethane gave the title compound as a white solid (4.23 g) m.p. 90°-93° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 48 h
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a pale yellow solid
  6. washChromatography eluting with dichloromethane

Sources & evidence

ORD record
ord-0dcdab110f0f46959854301c623b7893
Source dataset
uspto-grants-1994_12
Patent number
US05374646

Reaction notes

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