반응 #82589

반응 방정식

CaCl2

H2O

2-nitro-3,4,5,6-tetrafluoroaniline

benzene

→

3,4,5,6-Tetrafluoro-1,2-diaminobenzene

용매

EtOH

EtOH

EtOAc

반응 조건

후처리

1. 1
   온도was heated m
2. 2
   온도reflux
3. 3
   온도The reaction mixture was refluxed 5 h
4. 4
   기타The Zn was removed by vacuum filtration
5. 5
   세척the Zn rinsed with EtOH (30 mL)
6. 6
   기타The solvent was rotary evaporated
7. 7
   workup.DISSOLUTIONthe residue was dissolved in 20 mL Et2O
8. 8
   세척the solution washed with 2×15 mL H2O and 15 mL
9. 9
   건조The organic layer was dried (MgSO4) and vacuum
10. 10
    여과filtered
11. 11
    기타The solvent was rotary evaporated

실험 절차

3,4,5,6-Tetrafluoro-1,2-diaminobenzene was prepared using an adaptation of the method of Tsuji et al., J. Org. Chem. 55:580 (1990). A suspension of Zn powder (1.95 g, 29.8 mmol), CaCl2 (195 mg) and H2O (2.3 mL) in 7 mL EtOH was heated m reflux with stirring under N2. To this was added slowly dropwise a solution of 2-nitro-3,4,5,6-tetrafluoroaniline (2 g, 12.8 mmol) in 5 mL EtOH. The reaction mixture was refluxed 5 h. TLC analysis (silica gel, 2:1 benzene:EtOAc) indicated complete disappearance of the starting material. The Zn was removed by vacuum filtration, and the Zn rinsed with EtOH (30 mL). The solvent was rotary evaporated and the residue was dissolved in 20 mL Et2O and the solution washed with 2×15 mL H2O and 15 mL sat'd NaCl. The organic layer was dried (MgSO4) and vacuum filtered. The solvent was rotary evaporated to yield 396.6 mg (92.5%) of a purple brown solid, mp 120°-125° C., that was used without further purification.

출처