반응 #61205

반응 방정식

methanol

p-toluenesulfonic acid

N-iodosuccinimide

N-iodosuccinimide

p-toluenesulfonic acid

5-Amino-2-nitrobenzotrifluoride

→

title compound

2-Iodo-4-nitro-5-trifluoromethyl-phenylamine

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGthe solution stirred overnight at room temperature under nitrogen
2. 2
   농축The solution was concentrated under vacuum to a small volume
3. 3
   workup.ADDITIONWater (200 mL) was added to the reaction mixture
4. 4
   기타a brown solid precipitated out
5. 5
   여과The solid was filtered-
6. 6
   세척washed with water
7. 7
   workup.DISSOLUTIONdissolved in ethyl acetate (100 mL)
8. 8
   세척The organic solution was washed with 10% sodium thiosulfate solution (50 mL)
9. 9
   workup.ADDITIONby adding diethy
10. 10
    여과ether and water and filtering undissolved material
11. 11
    기타The layers were separated
12. 12
    세척the organic layer was washed with 10% sodium thiosulfate solution (50 mL), water
13. 13
    workup.ADDITIONwas then added to the aqueous layer
14. 14
    기타the layers separated
15. 15
    세척The organic layer was washed with brine (50 mL)
16. 16
    건조dried over magnesium sulfate
17. 17
    여과filtered
18. 18
    기타evaporated

실험 절차

5-Amino-2-nitrobenzotrifluoride (16.25 g, 78.8 mmol) was dissolved in tetrahydrofuran (100 mL) and methanol (100 mL) and to this solution was added p-toluenesulfonic acid (0.18 g, 0.95 mmol) and N-iodosuccinimide (17.8 g, 78.8 mmol). The solution was stirred all day. N-iodosuccinimide (0.78 g, 3.47 mmol) and p-toluenesulfonic acid (0.2 g, 1.05 mmol) were then added and the solution stirred overnight at room temperature under nitrogen. The solution was concentrated under vacuum to a small volume. Water (200 mL) was added to the reaction mixture and and a brown solid precipitated out. The solid was filtered- and washed with water, then dissolved in ethyl acetate (100 mL) and diethyl ether (60 mL). The organic solution was washed with 10% sodium thiosulfate solution (50 mL). This created an emulsion which was alleviated by adding diethy! ether and water and filtering undissolved material. The layers were separated and the organic layer was washed with 10% sodium thiosulfate solution (50 mL), water was then added to the aqueous layer and the layers separated. The organic layer was washed with brine (50 mL), dried over magnesium sulfate, filtered, and evaporated to yield the title compound as a brown solid that was dried under vacuum.

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