Réaction #1011319

Équation de réaction

aniline

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

NaHCO3

→

title compound

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

Solvants

DMF

Et2O

Conditions de réaction

Traitement

1. 1
   AutreThe vial was sealed
2. 2
   TempératureAfter cooling at RT
3. 3
   Lavagewashed with NaHCO3 10% and brine
4. 4
   Séchagedried over MgSO4
5. 5
   Autrethe solvent was evaporated off
6. 6
   Autreto give a residue which
7. 7
   Autrewas 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
   Autrethe MeCN was evaporated off under reduced pressure
10. 10
    Autreto give an aq. phase which
11. 11
    Extractionextracted with Et2O
12. 12
    SéchageThe combined extracts were dried over MgSO4
13. 13
    Autrethe solvent was evaporated off under reduced pressure

Mode opératoire

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]+.

Source