反応 #6688

反応方程式

2,3-difluoro-4-(4-pentyloxybutoxy)phenylboronic acid

2,3-Difluoro-4-(4-pentyloxybutoxy)phenylboronic acid

4-bromo-benzoic acid ethyl ester

4-Benzyloxybenzoic acid

sodium carbonate

→

2′,3′-difluoro-4′-(4-pentyloxybutoxy)-biphenyl-4-carboxylic acid ethyl ester

収率 88.0%

溶媒

water toluene

反応条件

後処理

1. 1
   抽出extracted with ethyl acetate:hexane(1:1)
2. 2
   洗浄washed with brine
3. 3
   乾燥dried over MgSO4
4. 4
   濃縮concentrated in vacuo
5. 5
   その他The purification by chromatography
6. 6
   その他on silica gel (5% EtOAc/hexanes) and recrystallization from acetonitrile

実験手順

A biphasic solution of 2,3-difluoro-4-(4-pentyloxybutoxy)phenylboronic acid (25): (1 equi.), 4-bromo-benzoic acid ethyl ester (12), (1 equi.), sodium carbonate (2.7 equi.), and Pd(PPh3)4 catalyst (0.01 equi.) in water-toluene (1:1) (2 mL/mmole) was stirred at 100 C. temperature for 12 h., cooled to room temperature, extracted with ethyl acetate:hexane(1:1), washed with brine, dried over MgSO4, and concentrated in vacuo. The purification by chromatography on silica gel (5% EtOAc/hexanes) and recrystallization from acetonitrile afforded 2′,3′-difluoro-4′-(4-pentyloxybutoxy)-biphenyl-4-carboxylic acid ethyl ester (26) as a white solid (88%).

出典