Ethanol → 3-Ethenyl-6-fluoro-2-methylbenzonitrile

HRID 1501986Notes

Reaction equation

HRID 1501986 reaction equation
Br[C:2]1[C:3]([CH3:11])=[C:4]([C:7]([F:10])=[CH:8][CH:9]=1)[C:5]#[N:6].[CH2:12](O)[CH3:13]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH:12]([C:2]1[C:3]([CH3:11])=[C:4]([C:7]([F:10])=[CH:8][CH:9]=1)[C:5]#[N:6])=[CH2:13]

Participants

4

Reactant 2

HCID 702EthanolHCID 666438523-Bromo-6-fluoro-2-methylbenzonitrile

Product 1

HCID 666438663-Ethenyl-6-fluoro-2-methylbenzonitrile

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Procedure

3-Bromo-6-fluoro-2-methylbenzonitrile (23.6 g, 110 mmol), potassium vinyl trifluoroborate (29.5 g, 221 mmol), PdCl2(dppf)-CH2Cl2 Adduct (4.03 g, 5.51 mmol), and TEA (30.7 mL, 221 mmol) were added to 250 mL of ethanol. The reaction mixture was degassed then stirred at reflux for 4 h. LC-MS confirmed the presence of product. The reaction mixture was diluted with ethyl acetate, washed twice with brine, dried, and evaporated to dryness. The crude material was then purified by MPLC chromatography using a 330 g Redi-sep column and eluting with a 10% EtOAc/Hexane solvent system to yield 3-ethenyl-6-fluoro-2-methylbenzonitrile.

Workup

  1. customThe reaction mixture was degassed
  2. temperatureat reflux for 4 h
  3. additionThe reaction mixture was diluted with ethyl acetate
  4. washwashed twice with brine
  5. customdried
  6. customevaporated to dryness
  7. customThe crude material was then purified by MPLC chromatography
  8. washeluting with a 10% EtOAc/Hexane solvent system

Sources & evidence

ORD record
ord-5e2f7dd6699e4d5292381229b03c7cc4
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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