反应详情

N-bromosuccinimide (1.04 g) and 2,2′-azobis(isobutylnitrile) (30 mg) were added to the carbon tetrachloride solution (7 ml) of 2-(4-bromo-3-methylphenyl)-2-methylpropionitrile (1.26 g) and then the solution was refluxed with heating for an hour. The solution was cooled on ice, then after removing the insoluble substances by filtration, the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in ethanol (10 ml) and water (1 ml) and a solution of potassium cyanide (0.41 g) was added to the solution. The reaction mixture was stirring overnight at room temperature. To the reaction mixture was added the ice-cold water and ethyl acetate, and the organic layer was separated. The obtained organic layer was sequentially washed with water (twice) and brine. After drying over anhydrous magnesium sulfate, the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier; Wakogel™ C-200; elution solvent; heptane:ethyl acetate, 19:1→5:1) to obtain the title compound. (917 mg) The property values of the obtained compound are as follows; 1H-NMR (CDCl3) δ (ppm): 1.74 (s, 6H), 3.87 (s, 2H), 7.38 (dd, J=8.4, 2.4 Hz, 1H), 7.57 (d, J=2.4 Hz, 1H), 7.64 (d, J=8.4 Hz, 1H).

1. temperaturethe solution was refluxed
2. temperaturewith heating for an hour
3. temperatureThe solution was cooled on ice
4. customafter removing the insoluble substances
5. filtrationby filtration
6. concentrationthe filtrate was concentrated under reduced pressure
7. dissolutionThe obtained residue was dissolved in ethanol (10 ml)
8. additionwater (1 ml) and a solution of potassium cyanide (0.41 g) was added to the solution
9. additionTo the reaction mixture was added the ice-cold water and ethyl acetate
10. customthe organic layer was separated
11. washThe obtained organic layer was sequentially washed with water (twice) and brine
12. dry with materialAfter drying over anhydrous magnesium sulfate
13. concentrationthe organic layer was concentrated under reduced pressure
14. customThe residue was purified by silica gel column chromatography (carrier; Wakogel™ C-200; elution solvent; heptane:ethyl acetate, 19:1→5:1)