反応 #61205

反応方程式

methanol

p-toluenesulfonic acid

N-iodosuccinimide

N-iodosuccinimide

p-toluenesulfonic acid

5-Amino-2-nitrobenzotrifluoride

→

title compound

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

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   workup.STIRRINGthe solution stirred overnight at room temperature under nitrogen
2. 2
   濃縮The solution was concentrated under vacuum to a small volume
3. 3
   workup.ADDITIONWater (200 mL) was added to the reaction mixture
4. 4
   その他a brown solid precipitated out
5. 5
   ろ過The solid was filtered-
6. 6
   洗浄washed with water
7. 7
   workup.DISSOLUTIONdissolved in ethyl acetate (100 mL)
8. 8
   洗浄The organic solution was washed with 10% sodium thiosulfate solution (50 mL)
9. 9
   workup.ADDITIONby adding diethy
10. 10
    ろ過ether and water and filtering undissolved material
11. 11
    その他The layers were separated
12. 12
    洗浄the organic layer was washed with 10% sodium thiosulfate solution (50 mL), water
13. 13
    workup.ADDITIONwas then added to the aqueous layer
14. 14
    その他the layers separated
15. 15
    洗浄The organic layer was washed with brine (50 mL)
16. 16
    乾燥dried over magnesium sulfate
17. 17
    ろ過filtered
18. 18
    その他evaporated

実験手順

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.

出典