反应 #833534

反应方程式

Iodobenzene

1,10-Phenanthroline

benzimidazole

cesium carbonate

→

1-Phenyl benzoimidazole

收率 45.0%

溶剂

dimethylformamide

hexane

反应条件

后处理

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

实验过程

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.

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