Réaction #792205

Équation de réaction

4-phenyl-1H-imidazole

2-bromothiophene

K2CO3

→

4-phenyl-1-(thiophen-2-yl)-1H-imidazole

Rendement 3.0%

Solvants

ethyl acetate

dioxane

Conditions de réaction

Traitement

1. 1
   Filtrationfiltered
2. 2
   ConcentrationThe filtrate was concentrated
3. 3
   Autrepurified by column chromatography

Mode opératoire

A suspension of 4-phenyl-1H-imidazole (500 mg, 3.47 mmol), 2-bromothiophene (0.4 ml, 4.16 mmol), CuI (131.9 mg, 0.694 mmol, trans-N,N′-dimethylcyclohexanediamine (0.08 ml, 0.694 mmol), and K2CO3 (1.43 g, 10.4 mmol) in dioxane (5 ml) was heated at 110° C. in a sealed tube for 16 hours. The reaction mixture was then diluted with ethyl acetate and filtered. The filtrate was concentrated and purified by column chromatography using 15-20% ethyl acetate/hexanes to yield the desired 4-phenyl-1-(thiophen-2-yl)-1H-imidazole (23 mg, 3%). The HPLC purity of the final product was 99.7%. LC-MS [M+H] 227 (C13H10N2S+H expected 227.06).

Source