반응 #1973897

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Ethyl 4-iodobenzoate

4-ethoxy-2,3-difluorophenylboronic acid

potassium carbonate

→

ethyl 4-ethoxy-2,3-difluoro-4′-biphenylbenzoate

수율 108.6%

용매

toluene

water

water

ethanol

toluene

반응 조건

후처리

1. 1
   온도heated
2. 2
   온도to reflux for 2 hours
3. 3
   workup.ADDITIONmixed with them
4. 4
   기타had separated into two phases of organic and aqueous phases
5. 5
   추출the extraction into an organic phase
6. 6
   기타The resulting organic phase was separated
7. 7
   세척washed with water
8. 8
   건조dried over anhydrous magnesium sulfate
9. 9
   농축The solution was concentrated under reduced pressure
10. 10
    기타the resulting residue was purified by column chromatography
11. 11
    기타The product was further purified by recrystallization from ethanol
12. 12
    기타dried

실험 절차

Ethyl 4-iodobenzoate (1) (25.0 g), 4-ethoxy-2,3-difluorophenylboronic acid (2) (20.1 g), potassium carbonate (25.0 g), Pd/C (0.25 g), toluene (100 ml), ethanol (100 ml) and water (100 ml) were added to a reaction vessel under an atmosphere of nitrogen, and heated to reflux for 2 hours. After the reaction solution had been cooled to 25° C., it was poured into water (500 ml) and toluene (500 ml), and mixed with them. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and the extraction into an organic phase was carried out. The resulting organic phase was separated, and washed with water, and then dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the resulting residue was purified by column chromatography using silica gel as a stationary phase powder and toluene as an eluent. The product was further purified by recrystallization from ethanol and dried to give ethyl 4-ethoxy-2,3-difluoro-4′-biphenylbenzoate (3) (18.8 g). The yield based on the compound (1) was 67.9%.

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