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

HRID 2175857Notes

Reaction equation

HRID 2175857 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.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:10]([C:2]1[C:3]([CH3:9])=[C:4]([C:7]#[N:8])[S:5][CH:6]=1)=[CH2:11]

Participants

5

Reactant 2

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

Product 1

HCID 86727075HCID 86727075, 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-3-methylthiophene-2-carbonitrile (3.00 g, 14.8 mmol), potassium vinyltrifluoroborate (2.40 g, 17.8 mmol) and Pd(dppf)Cl2 (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-c7134f5583e944e6a5fee4682a7bc6b9
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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