Hydrochloric Acid → 4-Fluoro-2-vinyl-benzonitrile

HRID 1172680Notes

Reaction equation

HRID 1172680 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]=[CH2:10].[Cu][C:12]#[N:13].Cl>CN(C)C=O>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:12]#[N:13])=[C:3]([CH:9]=[CH2:10])[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 112410891-Bromo-2-ethenyl-4-fluorobenzeneHCID 178418546HCID 178418546, compound

Product 1

HCID 595563374-Fluoro-2-vinyl-benzonitrileYield 60.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
200 °C

Procedure

4.0 g 1-Bromo-4-fluoro-2-vinyl-benzene and 1.87 g copper (I) cyanide were dissolved in 16 ml dimethylformamide and heated under microwave irradiation at 200° C. for 25 minutes. The cooled reaction mixture was poured into 200 ml 1 M HCl and extracted five times with portions of 60 ml ethyl acetate. The combined organic layers were washed with 100 ml 1 N HCl, dried over MgSO4, then the solvent was removed in vacuo and the resulting residue purified on silica gel with the eluent heptane=>n-heptane:ethyl acetate=6:1 to obtain 1.77 g 4-Fluoro-2-vinyl-benzonitrile as a solid.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted five times with portions of 60 ml ethyl acetate
  3. washThe combined organic layers were washed with 100 ml 1 N HCl
  4. dry with materialdried over MgSO4
  5. customthe solvent was removed in vacuo
  6. customthe resulting residue purified on silica gel with the eluent heptane=>n-heptane

Sources & evidence

ORD record
ord-648738f4cfc844d3bb6e1357344967f6
Source dataset
uspto-grants-2010_11
Patent number
US07834030B2

Reaction notes

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