Potassium vinyltrifluoroborate → HCID 86727086, compound

HRID 2175872Notes

Reaction equation

HRID 2175872 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[C:3]=1[CH3:11].[CH:12]([B-](F)(F)F)=[CH2:13].[K+]>CCO.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]>[CH:12]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[C:3]=1[CH3:11])=[CH2:13]

Participants

5

Reactant 2

HCID 23679353Potassium vinyltrifluoroborateHCID 595569134-Bromo-2-fluoro-3-methylbenzonitrile

Product 1

HCID 86727086HCID 86727086, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-bromo-2-fluoro-3-methylbenzonitrile (7.00 g, 32.7 mmol), potassium vinyltrifluoroborate (5.3 g, 39 mmol) and Pd(dppf)Cl2 (0.5 g, 0.7 mmol) in 70 mL of EtOH and 30 mL of TEA was refluxed under Ar for 4 hours. Concentrated, the residue was purified by column chromatography (petrol ether:EtOAc=10:1) to afford 4-ethenyl-2-fluoro-3-methylbenzonitrile.

Workup

  1. temperaturewas refluxed under Ar for 4 hours
  2. concentrationConcentrated
  3. customthe residue was purified by column chromatography (petrol ether:EtOAc=10:1)

Sources & evidence

ORD record
ord-957b214c939c4e36af44a59a50adafc2
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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