반응 #356219

반응 방정식

HCl

4-bromo-6-trifluoromethyl-pyran-2-one

4-Bromo-6-trifluoromethyl-pyran-2-one

4-iodobenzotrifluoride

isopropylmagnesium chloride

→

solid

수율 100.6%

6-Trifluoromethyl-4-(4-trifluoromethyl-phenyl)-pyran-2-one

수율 100.6%

용매

THF

반응 조건

후처리

1. 1
   기타the internal temperature below −65° C.
2. 2
   기타the cooling bath was removed
3. 3
   기타to reach 23° C.
4. 4
   workup.STIRRINGstirred at 23° C. for 35 min
5. 5
   기타were added at 23° C.
6. 6
   workup.STIRRINGstirring
7. 7
   workup.WAITwas continued at 23° C. for 30 min
8. 8
   기타[slightly exothermic reaction
9. 9
   기타rose to 45° C.
10. 10
    추출extracted with EtOAc
11. 11
    세척washed with sat. NaHCO3-sol
12. 12
    건조and brine, dried over Na2SO4
13. 13
    기타evaporated
14. 14
    기타dried at HV

실험 절차

To a solution of commercially available 4-iodobenzotrifluoride (1.36 g, 5.00 mmol) in THF (13 mL) at −78° C. was added isopropylmagnesium chloride (2 M in THF, 2.63 mL, 5.25 mmol) within 2 min keeping the internal temperature below −65° C., stirring was continued at −78 to −20° C. for 60 min. ZnCl2 (1 M in THF, 5.50 mL, 5.50 mmol) was added, the cooling bath was removed, the mixture was allowed to reach 23° C. and stirred at 23° C. for 35 min. Pd(PPh3)4 (58 mg, 1 mol %) and 4-bromo-6-trifluoromethyl-pyran-2-one (example C.22 step 3) (1.22 g, 5.00 mmol) were added at 23° C. and stirring was continued at 23° C. for 30 min [slightly exothermic reaction; internal temperature rose to 45° C.]. Poured into icecold 0.5 M HCl, extracted with EtOAc, washed with sat. NaHCO3-sol. and brine, dried over Na2SO4, evaporated and dried at HV to give an orange solid (1.55 g), which was purified by MPLC to give the title compound as a yellow solid (1.27 g, 82%). MS (EI) [(M)t]; mp 52° C.

출처