反应详情

4-chlorophenylhydrazine hydrochloride (5.24 g, 29.27 mmol), 2-fluoro-5-iodobenzaldehyde (7.5 g, 30.00 mmol) and cesium carbonate (22.8 g, 69.98 mmol) was suspended in NMP (120 mL) and stirred at ambient temperature for 45 min. The temperature was raised to +160° C. and the reaction mixture was stirred for 1 h, the now black suspension was allowed to reach r.t. Water was added, the slurry was extracted with EtOAc (500 mL. The organic phase was washed with brine (2×). The brine fractions and waterphase was combined and back extracted once with EtOAc. This second EtOAc phase was washed with brine (2×) before combined with the previous EtOAc phase. The organic phases were dried over Na2SO4, filtered and evaporated. The black residue were dissolved in DCM/Heptane (=1/1) and filtered through a silica column, and the column was then further eluted with DCM/Heptane (=1/1) solvent mixture. The fractions containing product was evaporated, residue was dissolved in EtOAc and Heptane was added, evaporation and diluting with Heptane afforded a slurry, the solid material was collected by filtration and washed with Heptane. Yield 2.82 g (27%)

1. temperatureThe temperature was raised to +160° C.
2. stirringthe reaction mixture was stirred for 1 h
3. customto reach r.t
4. extractionthe slurry was extracted with EtOAc (500 mL
5. washThe organic phase was washed with brine (2×)
6. extractionback extracted once with EtOAc
7. washThis second EtOAc phase was washed with brine (2×)
8. dry with materialThe organic phases were dried over Na2SO4
9. filtrationfiltered
10. customevaporated
11. dissolutionThe black residue were dissolved in DCM/Heptane (=1/1)
12. filtrationfiltered through a silica column
13. washthe column was then further eluted with DCM/Heptane (=1/1) solvent mixture
14. additionThe fractions containing product
15. customwas evaporated
16. dissolutionresidue was dissolved in EtOAc
17. additionHeptane was added
18. customevaporation
19. additiondiluting with Heptane
20. customafforded a slurry
21. filtrationthe solid material was collected by filtration
22. washwashed with Heptane