Potassium vinyltrifluoroborate → HCID 86727088, compound

HRID 2175880Notes

Reaction equation

HRID 2175880 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[C:3]=1[O:11][CH3:12].[CH:13]([B-](F)(F)F)=[CH2:14].[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]>[F:10][C:4]1[C:3]([O:11][CH3:12])=[C:2]([CH:13]=[CH2:14])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

5

Reactant 2

HCID 23679353Potassium vinyltrifluoroborateHCID 712707504-Bromo-2-fluoro-3-methoxybenzonitrile

Product 1

HCID 86727088HCID 86727088, 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-methoxybenzonitrile (6.0 g, 26 mmol), potassium vinyltrifluoroborate (4.20 g, 31.3 mmol) and Pd(dppf)Cl2 (0.8 g) in 60 mL of EtOH and 60 mL of TEA was refluxed under Ar for 4 hours. The resulting mixture was concentrated and the residue was purified by column chromatography (PE:EtOAc=20:1) to afford 2-fluoro-3-methoxy-4-vinylbenzonitrile.

Workup

  1. temperaturewas refluxed under Ar for 4 hours
  2. concentrationThe resulting mixture was concentrated
  3. customthe residue was purified by column chromatography (PE:EtOAc=20:1)

Sources & evidence

ORD record
ord-52bac4fe97fc45bb9097fc33f35e8fc9
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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