反应详情

To a stirring solution of 845 mg (3.72 mmol) of 3-bromo-5-nitrobenzonitrile in 5 mL of THF and 5 mL of EtOH was added 4.2 g (18.6 mmol) of SnCl2.2H2O in several portions. The reaction became slightly exothermic and was stirred at r.t. for about 12.5 h. The mixture was concentrated and 30 mL of 2 N NaOH was added. After the mixture was stirred for 2 h, H2O and EtOAc were added, and the organic layer was washed with 50 mL of H2O and 40 mL of brine. The aqueous layer was extracted with EtOAc and washed with brine. The combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (35% EtOAc/hexanes) provided 461 mg of 3-amino-5-bromobenzonitrile as a yellow solid in 63% yield.

1. concentrationThe mixture was concentrated
2. addition30 mL of 2 N NaOH was added
3. stirringAfter the mixture was stirred for 2 h
4. additionH2O and EtOAc were added
5. washthe organic layer was washed with 50 mL of H2O and 40 mL of brine
6. extractionThe aqueous layer was extracted with EtOAc
7. washwashed with brine
8. dry with materialThe combined extracts were dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customPurification by flash silica gel chromatography (35% EtOAc/hexanes)