反応 #84582

反応方程式

hydrochloric acid

4-bromo-1-chloro-2-fluorobenzene

acetylacetone

tripotassium phosphate

→

title compound

収率 48.3%

1-(4-chloro-3-fluorophenyl)propan-2-one

収率 48.3%

溶媒

DMSO

反応条件

後処理

1. 1
   温度The mixture was cooled to rt
2. 2
   抽出The resulting mixture was extracted with EtOAc (100 mL×3)
3. 3
   洗浄the combined organic phases were washed with brine (100 mL×2)
4. 4
   乾燥dried over anhydrous Na2SO4 (50 g)
5. 5
   ろ過filtered
6. 6
   濃縮The filtrate was concentrated in vacuo
7. 7
   その他The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=10:1)

実験手順

To a mixture of 4-bromo-1-chloro-2-fluorobenzene (20.90 g, 100.0 mmol) and acetylacetone (30 mL, 300.0 mmol) in DMSO (100 mL) were added tripotassium phosphate (63.70 g, 300.0 mmol) and CuI (3.00 g, 15.80 mmol) under N2 and the mixture was stirred at 110° C. for 23 h. The mixture was cooled to rt and hydrochloric acid (300 mL, 2 M) was added. The resulting mixture was extracted with EtOAc (100 mL×3) and the combined organic phases were washed with brine (100 mL×2), dried over anhydrous Na2SO4 (50 g), and filtered. The filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=10:1) to give the title compound as yellow liquid (9.02 g, 48.2%).

出典