Potassium Cyanide → 2,3-Difluorophenylacetonitrile

HRID 1826905Notes

Reaction equation

HRID 1826905 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-b006153201bf4905bdcff29ddbfe4b94
Source dataset
uspto-grants-2006_05
Patent number
US07053104B2

Reaction notes

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