Potassium Cyanide → 2-(4-Fluoro-3-phenoxyphenyl)acetonitrile

HRID 1588881Notes

Reaction equation

HRID 1588881 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C-:17]#[N:18].[K+]>O1CCCC1.O.O1CCOCCOCCOCCOCCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:17]#[N:18])=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 135636494-(Chloromethyl)-1-fluoro-2-phenoxybenzene

Product 1

HCID 111721992-(4-Fluoro-3-phenoxyphenyl)acetonitrileYield 113.2%

Reagents, catalysts & solvents 3

HCID 2855718-Crown-6CatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of 5.0 grams (0.021 mole) of 4-fluoro-3-phenoxyphenylmethyl chloride, 4.1 grams (0.063 mole) of potassium cyanide and 0.6 gram (0.002 mole) of 1,4,7,10,13,16-hexaoxacyclooctadecane in 180 ml of tetrahydrofuran was heated at reflux for about four hours. After this time the reaction mixture was diluted with 180 ml of water, and then extracted with two 100 ml portions of diethyl ether. The combined ether extracts were washed with five 200 ml portions of water. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 5.4 grams of 4-fluoro-3-phenoxyphenylacetonitrile. The nmr spectrum was consistent with the proposed structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for about four hours
  3. extractionextracted with two 100 ml portions of diethyl ether
  4. washThe combined ether extracts were washed with five 200 ml portions of water
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e172267c6d4043db96c530d17dcb3a40
Source dataset
uspto-grants-1993_06
Patent number
US05223536

Reaction notes

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