Potassium vinyltrifluoroborate → HCID 66643889, compound

HRID 1474336Notes

Reaction equation

HRID 1474336 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-364c0d07a4df451f8ff7d37e06028a4e
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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