反应详情

A mixture of 2-chloro-5-(methoxyethoxy)toluene (5.00 g; 26.8 mmol), N-bromosuccinimide (4.77 g; 26.8 mmol) and 2,2-azobis(isobutyronitrile) (0.09 g; 0.53 mmol) in carbon tetrachloride (25 ml) was refluxed for 2 hours. After air cooling and filtration the precipitate, the filtrate was condensed under reduced pressure. To the residue were added sodium cyanide (2.77 g; 80.4 mol) and anhydrous N,N-dimethylformamide (30 ml). The mixture was stirred at room temperature for 2 hours. Water and ethyl acetate were added to the reaction solution and extracted. The organic layer was washed with brine, dried over anhydrous sodium sulphate, and evaporated under reduced pressure. The residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=6:1→4:1) to give [2-chloro-5-(methoxymethoxy)phenyl]acetonitrile as colorless oil (2.64 g; 47%).

1. temperaturewas refluxed for 2 hours
2. temperatureAfter air cooling
3. filtrationfiltration the precipitate
4. customcondensed under reduced pressure
5. extractionextracted
6. washThe organic layer was washed with brine
7. dry with materialdried over anhydrous sodium sulphate
8. customevaporated under reduced pressure
9. customThe residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=6:1→4:1)