Reaction #165097

Reaction equation

5-nitro-2-thiophenecarbonitrile

p-cresol

potassium carbonate

→

title compound

Yield 78.9%

5-p-Tolyloxy-thiophene-2-carbonitrile

Yield 78.9%

Solvents

dimethyl sulfoxide

Conditions

Workup

1. 1
   TemperatureThe reaction solution was cooled to room temperature
2. 2
   Extractionextracted with ethyl acetate
3. 3
   workup.ADDITIONafter addition of water
4. 4
   WashThe organic layer was washed with saturated aqueous sodium chloride
5. 5
   Otherthe solvent was evaporated under a reduced pressure
6. 6
   OtherThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:3→2:1)

Procedure

To a dimethyl sulfoxide (100 mL) solution of 5-nitro-2-thiophenecarbonitrile (6.30 g, 40.9 mmol) were added p-cresol (8.85 g, 81.8 mmol) and potassium carbonate (11.3 g, 81.8 mmol) under nitrogen atmosphere, which was stirred for 5 hours at 60° C. The reaction solution was cooled to room temperature, and extracted with ethyl acetate after addition of water. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:3→2:1) to obtain the title compound (6.95 g, 78.9%).

Source