Реакция #72946

Уравнение реакции

2-bromo-4-(iodomethyl)thiazole

sodium cyanide

→

product

Выход 86.0%

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

Выход 86.0%

Растворители

diethyl ether water

DMSO

Условия реакции

Обработка

1. 1
   Другоеthe layers separated
2. 2
   Экстракцияthe aqueous was extracted further with ether (2×)
3. 3
   Промывкаthe combined organics washed with brine
4. 4
   Сушкаdried (Na2SO4)
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated
7. 7
   ДругоеThe resultant residue was purified by column chromatography (3:1 Petroleum ether/EtOAc)

Методика

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

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