反应详情

温度

90 °C

4-tert-Butyl-3-chloroaniline (690 mg, 3.8 mmol) was dissolved in 12 M sulfuric acid (30 ml) and then heated at 90° C. To the clear solution was added 5 ml of aqueous solution of sodium nitrite (776 mg, 11.3 mmol) at ambient temperature. The reaction mixture was stirred at ambient temperature for 15 minutes. Urea was added to the mixture until excess sodium nitrite was destroyed (by checking starch-iodine test paper). A small amount of cupric sulfate was added to the mixture and then the mixture was stirred at 90° C. for 30 minutes. The resulting organic layer was extracted with ethyl acetate washed with brine, dried over sodium sulfate. After filtration to separate solvent and sodium sulfate, the solvent was removed under reduced pressure to give a residue, which was applied to a silica gel chromatography column and eluted with ethyl acetate/hexane=¼ to furnish 0.44 g (64% yield) of the title compound as a brown oil.

1. customwas destroyed (by checking starch-iodine test paper)
2. additionA small amount of cupric sulfate was added to the mixture
3. stirringthe mixture was stirred at 90° C. for 30 minutes
4. extractionThe resulting organic layer was extracted with ethyl acetate
5. washwashed with brine
6. dry with materialdried over sodium sulfate
7. filtrationAfter filtration
8. customto separate solvent and sodium sulfate
9. customthe solvent was removed under reduced pressure
10. customto give a residue, which
11. washeluted with ethyl acetate/hexane=¼