반응 #84582

반응 방정식

hydrochloric acid

4-bromo-1-chloro-2-fluorobenzene

acetylacetone

tripotassium phosphate

→

title compound

수율 48.3%

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

수율 48.3%

용매

DMSO

반응 조건

후처리

1. 1
   온도The mixture was cooled to rt
2. 2
   추출The resulting mixture was extracted with EtOAc (100 mL×3)
3. 3
   세척the combined organic phases were washed with brine (100 mL×2)
4. 4
   건조dried over anhydrous Na2SO4 (50 g)
5. 5
   여과filtered
6. 6
   농축The filtrate was concentrated in vacuo
7. 7
   기타The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=10:1)

실험 절차

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%).

출처