反应详情

To a stirred solution of 1-bromo-3-(bromomethyl)-5-methylbenzene (6.56 kg, 0.1515 M) in ethanol (20 L) were added potassium cyanide (2.38 kg, 36.55 mol) and distilled water (10 L) in this order. The mixture was refluxed for 3 hours. After cooling to room temperature, the mixture was evaporated in vacuo and the residue was partitioned between ethyl acetate (30 L) and brine (20 L). The organic layer was dried with magnesium sulfate (2 kg) and concentrated under reduced pressure to give a brown-colored oil. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane, 1:9) to afford 3-bromo-5-methylbenzyl cyanide (2.06 kg, 9.81 mol, 39%) as a pale brown oil.

1. distillationdistilled water (10 L) in this order
2. temperatureThe mixture was refluxed for 3 hours
3. customthe mixture was evaporated in vacuo
4. customthe residue was partitioned between ethyl acetate (30 L) and brine (20 L)
5. dry with materialThe organic layer was dried with magnesium sulfate (2 kg)
6. concentrationconcentrated under reduced pressure
7. customto give a brown-colored oil
8. customThe crude product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane, 1:9)