반응 #160984

반응 방정식

aniline

1-chloro-1,1,2,2-tetrafluoro-2-iodoethane

NaHCO3

→

title compound

4-(2-Chloro-1,1,2,2-tetrafluoroethyl)aniline

용매

DMF

Et2O

반응 조건

후처리

1. 1
   기타The vial was sealed
2. 2
   온도After cooling at RT
3. 3
   세척washed with NaHCO3 10% and brine
4. 4
   건조dried over MgSO4
5. 5
   기타the solvent was evaporated off
6. 6
   기타to give a residue which
7. 7
   기타was purified by flash chromatography (RediSep® Silica gel column, n-heptane/EtOAc, from 0 to 25% EtOAc) and further by reverse phase chromatography (MPLC, Lichroprep® 15-25 μm column, eluents: water+0.1% formic/MeCN+0.1% formic acid, gradient 10 to 50% MeCN+0.1% formic acid)
8. 8
   workup.ADDITIONThe fractions containing pure product
9. 9
   기타the MeCN was evaporated off under reduced pressure
10. 10
    기타to give an aq. phase which
11. 11
    추출extracted with Et2O
12. 12
    건조The combined extracts were dried over MgSO4
13. 13
    기타the solvent was evaporated off under reduced pressure

실험 절차

Ni(PPh3)4 (222 mg, 0.2 mmol) was added to a mixture of aniline (745 mg, 8 mmol) and 1-chloro-1,1,2,2-tetrafluoro-2-iodoethane (1049 mg, 4 mmol) in DMF (10 mL) in a MW vial under an argon atmosphere. The vial was sealed and the RM was stirred for two days at 80° C. After cooling at RT, the RM was dissolved in Et2O, washed with NaHCO3 10% and brine, dried over MgSO4 and the solvent was evaporated off under reduce pressure to give a residue which was purified by flash chromatography (RediSep® Silica gel column, n-heptane/EtOAc, from 0 to 25% EtOAc) and further by reverse phase chromatography (MPLC, Lichroprep® 15-25 μm column, eluents: water+0.1% formic/MeCN+0.1% formic acid, gradient 10 to 50% MeCN+0.1% formic acid). The fractions containing pure product were combined and the MeCN was evaporated off under reduced pressure to give an aq. phase which was neutralized with NaHCO3 and extracted with Et2O. The combined extracts were dried over MgSO4 and the solvent was evaporated off under reduced pressure to afford the title compound as a red oil. HPLC (Condition 4) tR=5.48 min, UPLC-MS (Condition 3) tR=1.04 min, m/z=269 [M+H]+.

출처