반응 #1933191

반응 방정식

2-(2-methoxy-4-(methylsulfonyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

5-bromo-2-fluoro-iodobenzene

Na2CO3

→

title compound

수율 71.0%

5′-Bromo-2′-fluoro-2-methoxy-4-(methylsulfonyl)-1,1′-biphenyl

수율 71.0%

용매

dioxane

water

반응 조건

후처리

1. 1
   기타the reaction mixture was degassed again
2. 2
   온도before cooling to room temperature
3. 3
   농축concentrating under reduced pressure
4. 4
   기타The residue was partitioned between water (100 mL) and EtOAc (100 mL)
5. 5
   기타The organic phase was separated
6. 6
   추출the aqueous layer was re-extracted with EtOAc (2×100 mL)
7. 7
   건조The combined organic layers were dried (Na2SO4)
8. 8
   여과filtered
9. 9
   농축concentrated under reduced pressure
10. 10
    기타to give the crude
11. 11
    기타The crude was purified by silica gel column chromatography
12. 12
    세척eluting with 10-30% EtOAc/heptane

실험 절차

A solution of 2-(2-methoxy-4-(methylsulfonyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Preparation 16, 3.04 g, 9.74 mmol), 5-bromo-2-fluoro-iodobenzene (2.66 g, 8.85 mmol), and Na2CO3 (2.80, 26.55 mmol) in dioxane (60 mL) and water (15 mL) was degassed, tetrakis(triphenylphosphine)palladium(0) was added and the reaction mixture was degassed again. The reaction mixture was heated at 110° C. for 3 hours before cooling to room temperature and concentrating under reduced pressure. The residue was partitioned between water (100 mL) and EtOAc (100 mL). The organic phase was separated and the aqueous layer was re-extracted with EtOAc (2×100 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure to give the crude. The crude was purified by silica gel column chromatography eluting with 10-30% EtOAc/heptane to afford the title compound in 71% yield, 2.25 g.

출처