Water → 3-Nitrophenylacetonitrile

HRID 1256076Notes

Reaction equation

HRID 1256076 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1.[C-:12]#[N:13].[Na+].O>CN(C=O)C>[N+:9]([C:5]1[CH:4]=[C:3]([CH2:2][C:12]#[N:13])[CH:8]=[CH:7][CH:6]=1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 77568Benzene, 1-(bromomethyl)-3-nitro-

Product 1

HCID 121253-NitrophenylacetonitrileYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(bromomethyl)-3-nitrobenzene (30 g, 0.139 mol) and NaCN (10.21 g, 0.208 mol) in DMF (150 mL) was stirred at 50° C. for 5 hrs. The mixture was poured into water and extracted with ethyl acetate. The combined organic layer were dried, concentrated and purified by silica-gel column chromatography (PE:EA 20:1˜6:1) to give compound 2-(3-nitrophenyl)acetonitrile (9.9 g, yield 44%).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe combined organic layer were dried
  3. concentrationconcentrated
  4. custompurified by silica-gel column chromatography (PE:EA 20:1˜6:1)

Sources & evidence

ORD record
ord-726313acd1234971b02d494a3ea72bf8
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

Loading…