반응 #48060

반응 방정식

4-bromo-2-chloropyridine

(trimethylsilyl)acetylene

→

2-chloro-4-trimethylsilanylethynyl-pyridine

수율 91.0%

용매

triethylamine

반응 조건

후처리

1. 1
   기타The triethylamine was then removed in vacuo, water
2. 2
   workup.ADDITIONwas added
3. 3
   추출the mixture was extracted with diethylether
4. 4
   세척The combined organic extracts were then washed with water and brine
5. 5
   건조dried (Na2SO4)
6. 6
   여과filtered
7. 7
   농축concentrated in vacuo
8. 8
   기타to give a residue which
9. 9
   기타was purified by column chromatography (heptane/EtOAc 100:0 to 98:2)

실험 절차

A mixture of 2.5 g of 4-bromo-2-chloropyridine (12.6 mmol), 2.2 ml of (trimethylsilyl)acetylene (15.1 mmol), 153 mg of copper(I)iodide (0.79 mmol) and 287 mg of bis(triphenylphosphine)palladium(II)chloride (0.41 mmol) in triethylamine (15 ml) was stirred at RT for 1 h. The triethylamine was then removed in vacuo, water was added and the mixture was extracted with diethylether. The combined organic extracts were then washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo to give a residue which was purified by column chromatography (heptane/EtOAc 100:0 to 98:2) to give 2-chloro-4-trimethylsilanylethynyl-pyridine (2.394 g, 91%) as a light yellow liquid. MS (ISP) 210.1 (M+H)+.

출처