반응 #1933232

반응 방정식

2-(4-(ethylsulfonyl)-2-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

4-chloro-1-fluoro-2-iodobenzene

sodium carbonate

→

title compound

수율 28.0%

5′-Chloro-4-(ethylsulfonyl)-2,2′-difluoro-1,1-biphenyl

수율 28.0%

용매

dioxane

water

반응 조건

후처리

1. 1
   기타the mixture was degassed twice more
2. 2
   온도The reaction was cooled
3. 3
   workup.ADDITIONdiluted with EtOAc (50 mL) and water (50 mL)
4. 4
   기타the layers separated
5. 5
   추출the aqueous extracted with EtOAc (2×30 mL)
6. 6
   세척The combined organic layers were washed with brine (30 mL)
7. 7
   건조dried over MgSO4
8. 8
   기타the solvent removed in vacuo
9. 9
   기타The crude was purified by silica gel column chromatography
10. 10
    세척eluting with EtOAc:heptane 1:19 to 1:1

실험 절차

A solution of 2-(4-(ethylsulfonyl)-2-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Preparation 45, 1.77 g, 5.64 mmol), 4-chloro-1-fluoro-2-iodobenzene (1.28 g, 5.00 mmol), and sodium carbonate (1.59 g, 15.00 mmol) in dioxane (40 mL) and water (10 mL) was degassed. Tetrakis(triphenylphosphine)palladium(0) (577 mg, 0.50 mmol) was added and the mixture was degassed twice more, and the reaction warmed to 80° C. for 2 hours. The reaction was cooled and diluted with EtOAc (50 mL) and water (50 mL), the layers separated and the aqueous extracted with EtOAc (2×30 mL). The combined organic layers were washed with brine (30 mL), dried over MgSO4 and the solvent removed in vacuo. The crude was purified by silica gel column chromatography eluting with EtOAc:heptane 1:19 to 1:1 to give the title compound as a colourless oil 28% yield, 443 mg.

출처