Potassium Cyanide → 2,3-Difluorophenylacetonitrile

HRID 2302061Notes

Reaction equation

HRID 2302061 reaction equation
[F:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.[C-:11]#[N:12].[K+]>C(#N)C.C(OCC)C.C1OCCOCCOCCOCCOCCOC1>[F:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][C:11]#[N:12]

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 5179841-(Bromomethyl)-2,3-difluoro-benzene

Product 1

HCID 5189682,3-DifluorophenylacetonitrileYield 100.1%

Reagents, catalysts & solvents 3

HCID 2855718-Crown-6CatalystHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

2,3-Difluorobenzyl bromide (5 g, 24.2 mmol) in acetonitrile (20 mL) was treated with 18-crown-6 (638 mg, 2.4 mmol) and potassium cyanide (5 g, 77 mmol). The reaction was heated at reflux for 5.5 hours. The reaction was diluted with diethyl ether (100 mL). The resulting organic solution was washed with 1 N NaOH (3×25 mL), dried over anhydrous MgSO4, filtered, and concentrated to afford 3.71 g of crude 2,3-difluorobenzyl cyanide.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 5.5 hours
  3. washThe resulting organic solution was washed with 1 N NaOH (3×25 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-85e514e2355c466d812bc9824f51c63f
Source dataset
uspto-grants-2002_08
Patent number
US06429207B1

Reaction notes

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