反応 #1973897

反応方程式

Ethyl 4-iodobenzoate

4-ethoxy-2,3-difluorophenylboronic acid

potassium carbonate

→

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

収率 108.6%

溶媒

toluene

water

water

ethanol

toluene

反応条件

後処理

1. 1
   温度heated
2. 2
   温度to reflux for 2 hours
3. 3
   workup.ADDITIONmixed with them
4. 4
   その他had separated into two phases of organic and aqueous phases
5. 5
   抽出the extraction into an organic phase
6. 6
   その他The resulting organic phase was separated
7. 7
   洗浄washed with water
8. 8
   乾燥dried over anhydrous magnesium sulfate
9. 9
   濃縮The solution was concentrated under reduced pressure
10. 10
    その他the resulting residue was purified by column chromatography
11. 11
    その他The product was further purified by recrystallization from ethanol
12. 12
    その他dried

実験手順

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%.

出典