Réaction #833534

Équation de réaction

Iodobenzene

1,10-Phenanthroline

benzimidazole

cesium carbonate

→

1-Phenyl benzoimidazole

Rendement 45.0%

Solvants

dimethylformamide

hexane

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONIn the dark, an oven-dried 50 ml round-bottomed flask containing a stir bar
2. 2
   AutreThe round-bottomed flask with the contents was sealed with septa
3. 3
   Autredegassed with argon for 15 minutes
4. 4
   AutreThe reaction mixture was degassed with argon for 30 minutes
5. 5
   TempératureThe reaction mixture was cooled to ambient temperature
6. 6
   Concentrationconcentrated in vacuo
7. 7
   workup.ADDITION10 ml of ethyl acetate was added into the concentrated reaction mixture
8. 8
   FiltrationIt was then filtered
9. 9
   Lavagewashed with 30 ml of ethyl acetate
10. 10
    ConcentrationThe filtrate was concentrated under vacuo
11. 11
    Autreto give the crude product
12. 12
    AutreThe crude product was purified by column chromatography on silica gel (40% ethyl acetate

Mode opératoire

In the dark, an oven-dried 50 ml round-bottomed flask containing a stir bar was charged with CuI (0.171 g, 0.1 eq.), benzimidazole (1.273 g, 1.2 eq.), and cesium carbonate (6.138 g, 2.1 eq.) respectively. The round-bottomed flask with the contents was sealed with septa and degassed with argon for 15 minutes. Iodobenzene (1 ml, 1 eq.), 1,10-Phenanthroline (0.323 g, 0.2 eq.), and dimethylformamide (25 ml) were then successively added into the round-bottomed flask under a continuous flow of argon. The reaction mixture was degassed with argon for 30 minutes. The reaction was stirred with heating via an oil bath at 110° C. for 24 hours in the dark under nitrogen. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. 10 ml of ethyl acetate was added into the concentrated reaction mixture. It was then filtered and washed with 30 ml of ethyl acetate. The filtrate was concentrated under vacuo to give the crude product. The crude product was purified by column chromatography on silica gel (40% ethyl acetate:60% hexane as the eluent) providing 0.780 g of 1-Phenyl benzoimidazole (45% yield) as yellow liquid.

Source