Diethyl Ether → 4-Bromo-3-methyl-2-thiophenecarbonitrile

HRID 2175856Notes

Reaction equation

HRID 2175856 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([Br:8])[C:6]=1[CH3:7].[C:9]([Cu])#[N:10].CCOCC>CN(C=O)C>[Br:8][C:5]1[C:6]([CH3:7])=[C:2]([C:9]#[N:10])[S:3][CH:4]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 148351682,4-Dibromo-3-methylthiopheneHCID 178418546HCID 178418546, compound

Product 1

HCID 217176714-Bromo-3-methyl-2-thiophenecarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,4-dibromo-3-methylthiophene (20.0 g, 78.1 mmol) and CuCN (6.30 g, 70.3 mmol) in 150 mL of DMF was stirred at reflux for 4 hours before cooling down. The reaction mixture was poured into 1 L of ether with stirring and the precipitate was removed by filtration. The filtrate was washed with water (3×100 mL), brine (100 mL), dried over anhydrous Na2SO4 and concentrated. The residue was purified by silica column chromatography (petrol ether: EtOAc=50:1) to afford 4-bromo-3-methylthiophene-2-carbonitrile.

Workup

  1. temperatureat reflux for 4 hours
  2. temperaturebefore cooling down
  3. stirringwith stirring
  4. customthe precipitate was removed by filtration
  5. washThe filtrate was washed with water (3×100 mL), brine (100 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica column chromatography (petrol ether: EtOAc=50:1)

Sources & evidence

ORD record
ord-0bd7ea83c9764b48981321519de566b6
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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