Sodium Cyanide → 3-Nitrophenylacetonitrile

HRID 1256152Notes

Reaction equation

HRID 1256152 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+]>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

4

Reactant 2

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

Product 1

HCID 121253-NitrophenylacetonitrileYield 55.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 1-(bromomethyl)-3-nitrobenzene (30 g, 0.14 mol) in DMF (200 mL) was heated to 70° C., then sodium cyanide (17 g, 0.21 mol) was added slowly. The reaction mixture was stirred at 70° C. for 5 hours. The reaction was terminated by addition of water. The aqueous layer was extracted with ethyl acetate 3 times. The combined organic phase was washed with brine, dried over sodium sulfate. The crude product was purified by silica gel column chromatography (petroleum ether/ethyl acetate=10:1) to give 2-(3-nitrophenyl)acetonitrile (12.5 g, yield 33%). 1H NMR: 400 MHz CDCl3 δ 8.15-8.14 (m, 2H), 7.66-7.64 (m, 1H), 7.56-7.52 (m, 1H), 3.82 (s, 2H).

Workup

  1. customThe reaction was terminated by addition of water
  2. extractionThe aqueous layer was extracted with ethyl acetate 3 times
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customThe crude product was purified by silica gel column chromatography (petroleum ether/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-d58438bda1b84041b37fc460922d21e6
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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