반응 #427249

반응 방정식

1-bromo-2-ethyl-5-fluoro-4-methoxy-benzene

SPhos

4,4,5,5-tetramethyl-1,3,2-dioxaborolane

triethylamine

→

title compound

수율 64.0%

2-(2-Ethyl-5-fluoro-4-methoxy-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

수율 64.0%

용매

dioxane

반응 조건

후처리

1. 1
   기타The reaction mixture was degassed with nitrogen
2. 2
   온도cooled to room temperature
3. 3
   여과filtered through a pad of Celite
4. 4
   세척washing with EtOAc
5. 5
   기타The solvent was removed in vacuo
6. 6
   workup.DISSOLUTIONthe residue was redissolved in EtOAc (30 mL)
7. 7
   세척washed with water (30 mL)
8. 8
   건조The organic layer was dried over sodium sulfate
9. 9
   농축concentrated in vacuo
10. 10
    기타The crude material was triturated with methanol
11. 11
    여과the resulting solid was collected by filtration

실험 절차

To a solution of 1-bromo-2-ethyl-5-fluoro-4-methoxy-benzene (Preparation 12, 18.0 g, 77.2 mmol) in dioxane (100 mL) were added SPhos (4.12 g, 10.0 mmol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (14.8 g, 116 mmol) and triethylamine (10.7 mL, 77.2 mmol). The reaction mixture was degassed with nitrogen prior to the addition of dichlorobis(acetonitrile)palladium (II) (801 mg, 3.09 mmol). The reaction mixture was then heated at 110° C. for 18 hours, cooled to room temperature and filtered through a pad of Celite, washing with EtOAc. The solvent was removed in vacuo and the residue was redissolved in EtOAc (30 mL) and washed with water (30 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude material was triturated with methanol and the resulting solid was collected by filtration to give the title compound as a beige solid (13.8 g) in a 64% yield.

출처