反応 #42783

反応方程式

ammonia

AlCl3

4-chlorophenylacetyl chloride

3-fluorophenol

→

title compound

2-(4-Chlorophenyl)-1-(4-fluoro-2-hydroxy-phenyl)-ethanone

溶媒

CH2Cl2

1,2-dichloroethane

反応条件

後処理

1. 1
   温度to warm to room temperature
2. 2
   温度heated at 90° C. for 16 h
3. 3
   温度The reaction mixture is cooled to room temperature
4. 4
   ろ過filtered through Celite
5. 5
   その他The organic phase is separated
6. 6
   洗浄washed with water, brine
7. 7
   乾燥dried (MgSO4)
8. 8
   その他The solvent is removed in vacuo
9. 9
   その他the crude product is purified by flash chromatography on silica gel

実験手順

To a solution of 4-chlorophenylacetyl chloride (27.6 g, 0.15 mol) in 1,2-dichloroethane (200 ml), cooled to 0° C. in an ice bath, under nitrogen is added slowly AlCl3 (21.8 g, 0.16 mol). The reaction mixture is stirred at 0° C. for 20 min. 3-fluorophenol (12.2 g, 0.11 mol) is added, and the reaction mixture is allowed to warm to room temperature, then heated at 90° C. for 16 h. The reaction mixture is cooled to room temperature, then poured cautiously into aqueous ammonia solution (500 ml) with vigourous stirring. The mixture is diluted with CH2Cl2 (250 ml) and filtered through Celite. The organic phase is separated, washed with water, brine and dried (MgSO4). The solvent is removed in vacuo, and the crude product is purified by flash chromatography on silica gel using iso-hexane:ethyl acetate (10:1 to 4:1) as the eluent to give the title compound.

出典