Dimethylformamide → 2-(3-Bromophenyl)-2-methylpropanenitrile

HRID 564015Notes

Reaction equation

HRID 564015 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH2:10][C:11]#N)[CH:7]=[CH:8][CH:9]=1.I[CH3:14].C[N:16]([CH:18]=O)C>C(OCC)C>[Br:3][C:4]1[CH:5]=[C:6]([C:10]([CH3:11])([CH3:14])[C:18]#[N:16])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 36023(3-Bromophenyl)acetonitrile

Product 1

HCID 105132942-(3-Bromophenyl)-2-methylpropanenitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

257 mg 95% sodium hydride were stirred at room temperature in 25 ml dry DMF under an atmosphere of nitrogen. A solution of 1 g 3-bromophenylacetonitrile and 1.593 g iodomethane in 10 ml dry diethyl ether was added slowly below 30° C. The mixture was stirred over night at room temperature and then quenched by addition of a small amount of water. The solvents were evaporated under vacuum and the residue was purified by chromatography on silica in a heptane/ethyl acetate gradient.

Workup

  1. customquenched by addition of a small amount of water
  2. customThe solvents were evaporated under vacuum
  3. customthe residue was purified by chromatography on silica in a heptane/ethyl acetate gradient

Sources & evidence

ORD record
ord-06100fb05b61410ea109aedc47e1e36e
Source dataset
uspto-grants-2011_11
Patent number
US08067599B2

Reaction notes

Loading…