반응 #72946

반응 방정식

2-bromo-4-(iodomethyl)thiazole

sodium cyanide

→

product

수율 86.0%

2-(2-bromothiazol-4-yl)ethanenitrile

수율 86.0%

용매

diethyl ether water

DMSO

반응 조건

후처리

1. 1
   기타the layers separated
2. 2
   추출the aqueous was extracted further with ether (2×)
3. 3
   세척the combined organics washed with brine
4. 4
   건조dried (Na2SO4)
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The resultant residue was purified by column chromatography (3:1 Petroleum ether/EtOAc)

실험 절차

A solution of 2-bromo-4-(iodomethyl)thiazole (2.11 g, 6.942 mmol) in DMSO (15 mL) under nitrogen was treated with sodium cyanide (345.0 mg, 7.039 mmol) and allowed to stir for 40 minutes. The reaction was diluted with diethyl ether/water and the layers separated, the aqueous was extracted further with ether (2×) and the combined organics washed with brine, dried (Na2SO4), filtered and concentrated. The resultant residue was purified by column chromatography (3:1 Petroleum ether/EtOAc) to afford the product as a white solid (1.20 g, 86% Yield). 1H NMR (CDCl3, 400 MHz) δ 3.91 (2H, s), 7.31 (1H, s); MS (ES+) 204.95

출처