反应详情

To a sulfuric acid (14 ml) —H2O (14 ml) solution of 3-chloro-4-(trifluoromethyl)aniline (1.96 g, 10 mmol) was added a H2O (10 mL) solution of sodium nitrite (828 mg,12 mmol) at 0 ° C. The reaction mixture was stirred at ambient temperature for 1 hour. The mixture was poured into 10 M sulfuric acid (50 mL). The stirred mixture was refluxed at 110 ° C. for 2 hours. The reaction mixture was then quenched with saturated aqueous solution of sodium bicarbonate and then crude products were extracted with ethyl acetate The organic layer was then washed with brine, dried over sodium sulfate. After the filtration to separate solvent and sodium sulfate, the solvent was removed under reduced pressure to give the residue, which was applied to a silica gel chromatography column and eluted with a ethyl acetate/hexane=⅓ to furnish 945 mg (48% yield) of the title compound as a brown oil.

1. temperatureThe stirred mixture was refluxed at 110 ° C. for 2 hours
2. customThe reaction mixture was then quenched with saturated aqueous solution of sodium bicarbonate
3. extractioncrude products were extracted with ethyl acetate The organic layer
4. washwas then washed with brine
5. dry with materialdried over sodium sulfate
6. filtrationAfter the filtration
7. customto separate solvent and sodium sulfate
8. customthe solvent was removed under reduced pressure
9. customto give the residue, which
10. washeluted with a ethyl acetate/hexane=⅓