4-Bromo-3-methyl-2-thiophenecarbonitrile → HCID 86727075, compound

HRID 1502027Notes

Reaction equation

HRID 1502027 reaction equation
Br[C:2]1[C:3]([CH3:9])=[C:4]([C:7]#[N:8])[S:5][CH:6]=1.[CH:10]([B-](F)(F)F)=[CH2:11].[K+]>CCO>[CH:10]([C:2]1[C:3]([CH3:9])=[C:4]([C:7]#[N:8])[S:5][CH:6]=1)=[CH2:11]

Participants

4

Reactant 2

HCID 217176714-Bromo-3-methyl-2-thiophenecarbonitrileHCID 23679353Potassium vinyltrifluoroborate

Product 1

HCID 86727075HCID 86727075, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-bromo-3-methylthiophene-2-carbonitrile (3.00 g, 14.8 mmol), potassium vinyltrifluoroborate (2.40 g, 17.8 mmol) and Pd (dppf)2Cl2 (0.5 g) in 30 mL of EtOH and 30 mL of TEA was refluxed under Ar for 4 hours. The reaction mixture was concentrated, and the residue was purified by column chromatography (petrol ether:EtOAc=50:1) to afford 4-ethenyl-3-methylthiophene-2-carbonitrile.

Workup

  1. temperaturewas refluxed under Ar for 4 hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by column chromatography (petrol ether:EtOAc=50:1)

Sources & evidence

ORD record
ord-9f3449544d7943e9984308a6d9bfa433
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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