反应详情

A solution of 4-fluoro phenylmagnesium bromide (3.76 g) in tetrahydrofuran (15ml) was added to a cooled solution of 2-chloromethyl-4-cyano-benzoyl chloride (3.95 g) in tetrahydrofuran (10 ml) so that the temperature did not raise above 0° C. The mixture was warmed slowly to room temperature and stirred over night. Saturated ammonium chloride solution (60 ml) was added and stirring continued for 0.5 hours. The phases were separated and the aqueous phase was extracted with diethylether (30 ml). The combined organic phases were dried over sodium sulfate, filtered and dried in vacuo to give a brown solid. Flash chromatography (ethyl acetate/n-hexane=1/10) provided the product as colourless solid. Yield 2.95 g, 58%. 1H NMR (CDCl3, 400 MHz): 4.71 (2H, s), 7.16-7.21 (2H, m), 7.46 (1H, d, J=7.9 Hz), 7.71 (1H, dd, J=1.5, 7.9 Hz), 7.81-7.86 (2H, m), 7.89 (1H, d, J=1.5 Hz). 13C NMR (CDCl3, 100 MHz): 42.3, 115.0, 116.4, 116.6, 117.9, 129.6, 132.95, 132.98, 133.4, 133.5, 134.3, 138.7, 142.4, 165.5, 168.1, 194.5.

1. temperaturedid not raise above 0° C
2. stirringstirring
3. customThe phases were separated
4. extractionthe aqueous phase was extracted with diethylether (30 ml)
5. dry with materialThe combined organic phases were dried over sodium sulfate
6. filtrationfiltered
7. customdried in vacuo
8. customto give a brown solid