Potassium vinyltrifluoroborate → HCID 66643889, compound

HRID 1187078Notes

Reaction equation

HRID 1187078 reaction equation
Br[C:2]1[C:3]([CH3:13])=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[C:7](=[O:12])[O:6][CH2:5]2.[CH:14]([B-](F)(F)F)=[CH2:15].[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:11][C:9]1[CH:10]=[C:2]([CH:14]=[CH2:15])[C:3]([CH3:13])=[C:4]2[C:8]=1[C:7](=[O:12])[O:6][CH2:5]2

Participants

5

Reactant 2

HCID 23679353Potassium vinyltrifluoroborateHCID 66643995HCID 66643995, compound

Product 1

HCID 66643889HCID 66643889, compound

Reagents, catalysts & solvents 2

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

Procedure

A mixture of 5-bromo-7-fluoro-4-methyl-3H-isobenzofuran-1-one (0.6 g, 2.45 mmol), potassium vinyltrifluoroborate (492 mg, 3.67 mmol) and Pd(dppf)Cl2 (100 mg) in 20 mL of TEA and 20 mL of EtOH was heated to reflux under N2 for 4 hrs and then concentrated. The resulting oil was purified by prep-TLC to give 7-fluoro-4-methyl-5-vinyl-3H-isobenzofuran-1-one.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2 for 4 hrs
  3. concentrationconcentrated
  4. customThe resulting oil was purified by prep-TLC

Sources & evidence

ORD record
ord-f98eb4c675b14d8c841f260106a614e5
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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