تفاعل #62350

معادلة التفاعل

(5-bromo-2-chlorothiophen-3-yl)methanol

dimethylformamide

→

title compound

5-Chloro-4-hydroxymethylthiophene-2-carbonitrile

المذيبات

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   غسيلthe organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine
2. 2
   تجفيفdried over anhydrous magnesium sulfate
3. 3
   أخرىthe solvent was evaporated
4. 4
   أخرىThe crude product was purified
5. 5
   أخرىseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-1:5)

الإجراء التجريبي

To a solution of 25.0 g (5-bromo-2-chlorothiophen-3-yl)methanol in 330 mL of dimethylformamide, 25.8 g of zinc cyanide (I) and 12.7 g tetrakis(triphenylphosphine)palladium(0) were added at room temperature, and stirred at 100° C. for 4 hours. Diluting with ethyl acetate, the organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-1:5), to afford 16.0 g of the title compound as colorless crystals.

المصدر