Reaktion #84218

Reaktionsgleichung

methanol

p-toluenesulfonic acid

N-iodosuccinimide

N-iodosuccinimide

p-toluenesulfonic acid

5-Amino-2-nitrobenzotrifluoride

→

title compound

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

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe solution stirred overnight at room temperature under nitrogen
2. 2
   EinengenThe solution was concentrated under vacuum to a small volume
3. 3
   workup.ADDITIONWater (200 mL) was added to the reaction mixture
4. 4
   Sonstigea brown solid precipitated out
5. 5
   FiltrationThe solid was filtered
6. 6
   Waschenwashed with water
7. 7
   workup.DISSOLUTIONdissolved in ethyl acetate (100 mL)
8. 8
   WaschenThe organic solution was washed with 10% sodium thiosulfate solution (50 mL)
9. 9
   workup.ADDITIONby adding diethyl ether and water
10. 10
    Filtrationfiltering undissolved material
11. 11
    SonstigeThe layers were separated
12. 12
    Waschenthe organic layer was washed with 10% sodium thiosulfate solution (50 mL), water
13. 13
    workup.ADDITIONwas then added to the aqueous layer
14. 14
    Sonstigethe layers separated
15. 15
    WaschenThe organic layer was washed with brine (50 mL)
16. 16
    Trocknendried over magnesium sulfate
17. 17
    Filtrationfiltered
18. 18
    Sonstigeevaporated

Vorschrift

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 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 diethyl 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.

Quelle