反应详情

2,3-Dichloro-5,6-dicyanohydroquinone (1.02 g, 4.50 mmol) was added to the solution of 4-fluoro-5-nitro-2,3-dihydro-indole (0.47 g, 2.25 mmol) in benzene (30 mL) and the mixture was refluxed for 7 h. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (100 mL) and water (100 mL). The organic phase was washed with water (3×10 mL), brine (3×10 mL), dried over anhydrous sodium sulphate and concentration in vacuo afforded the crude product. Purification by column chromatography over neutral alumina using 5% ethyl acetate in hexane as eluent afforded 1-ethyl-4-fluoro-5-nitro-indole (0.33 g, 72%) as yellow solid.

1. temperaturethe mixture was refluxed for 7 h
2. customThe solvent was removed in vacuo
3. customthe residue partitioned between ethyl acetate (100 mL) and water (100 mL)
4. washThe organic phase was washed with water (3×10 mL), brine (3×10 mL)
5. dry with materialdried over anhydrous sodium sulphate and concentration in vacuo
6. customafforded the crude product
7. customPurification by column chromatography over neutral alumina using 5% ethyl acetate in hexane as eluent