反应 #586153

ord-86dcc9b859f34b799c80b133dbbf25f6

反应方程式

OB(O)c1ccc(Cl)cc1Cl
2,4-dichlorophenylboronic acid
N#Cc1ccc(Br)cc1F
4-bromo-2-fluorobenzonitrile
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
Cc1ccccc1
toluene
N#Cc1ccc(-c2ccc(Cl)cc2Cl)cc1F
2-fluoro-4-(2,4-dichlorophenyl)benzonitrile
收率 94.0%

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    温度under reflux
  2. 2
    温度with heating for 2 hours
  3. 3
    workup.ADDITIONThe reaction mixture was poured into ice-cold water
  4. 4
    萃取extracted with toluene
  5. 5
    洗涤The toluene layer was washed with water twice
  6. 6
    干燥dried over anhydrous magnesium sulfate
  7. 7
    workup.DISTILLATIONThe solvent was distilled off under reduced pressure

实验过程

1.0 g (5.2 mmol) of 2,4-dichlorophenylboronic acid, 1.1 g (5.5 mmol) of 4-bromo-2-fluorobenzonitrile, 1.6 g (15.0 mmol) of sodium carbonate and 0.8 g (0.7 mmol) of tetrakis(triphenylphosphine) palladium were added to a solvent mixture of 50 ml of toluene, 25 ml of ethanol and 25 ml of water, and the reaction was carried out under reflux with heating for 2 hours. The reaction mixture was poured into ice-cold water and extracted with toluene. The toluene layer was washed with water twice and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.3 g of 2-fluoro-4-(2,4-dichlorophenyl)benzonitrile (yield 93.0%), which was used in Example 8 (1) as the starting material.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07767626B2uspto-grants-2010_08