Sodium Cyanide → 2-(2-Bromo-5-nitrophenyl)acetonitrile

HRID 1256096Notes

Reaction equation

HRID 1256096 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11]Br.[C-:13]#[N:14].[Na+]>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][C:13]#[N:14]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 109025011-Bromo-2-(bromomethyl)-4-nitrobenzene

Product 1

HCID 540611032-(2-Bromo-5-nitrophenyl)acetonitrileYield 34%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

A solution of 1-bromo-2-(bromomethyl)-4-nitrobenzene (54 g, 183 mmol) in toluene (200 mL) and water (100 mL) was heated to 60° C., then NaCN (27.2 g, 555 mmol) was added, followed by stirring at reflux overnight. Water was added to the mixture, 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=100:1 to 5:1) to give 2-(2-bromo-5-nitrophenyl)acetonitrile (15 g, yield 34%).

Workup

  1. temperatureat reflux overnight
  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=100:1 to 5:1)

Sources & evidence

ORD record
ord-db59144ff5884ec79fd6a5c2af9cd5a2
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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