反应 #2271694

反应方程式

3-Chloro-1-bromopropane

sodium hydride

2-aminophenol

water

→

2-(3 chloropropoxy) aniline

溶剂

dimethylformamide

dimethylformamide

dimethylformamide

反应条件

后处理

1. 1
   workup.ADDITIONunder nitrogen, was added
2. 2
   workup.ADDITIONAfter complete addition
3. 3
   workup.ADDITIONwas added
4. 4
   其他did not go above 8° C
5. 5
   workup.STIRRINGThe reaction was stirred for 4 hours
6. 6
   workup.WAITto stand at ambient temperature for 16 hours
7. 7
   萃取extracted with ethyl acetate
8. 8
   洗涤The ethyl acetate was washed (water)
9. 9
   干燥dried (MgSO4)
10. 10
    浓缩the solvent concentrated
11. 11
    其他to afford 25.4 g of a reddish, dark oil
12. 12
    其他About 12.0 g of the oil was chromatographed an HPLC columns

实验过程

To a stirred suspension of sodium hydride (11.0 g, 230 mmol of a 50% oil dispersion) in dimethylformamide (250 ml), under nitrogen, was added, dropwise, 2-aminophenol (25.0 g, 230 mmol) dissolved in dimethylformamide (125 ml). After complete addition, the reaction was stirred at ambient temperature for 1 hour, and then it was cooled to 5° C. (ice bath. 3-Chloro-1-bromopropane (36.2 g, 230 mmol) in dimethylformamide 50 ml) was added, dropwise, so that the temperature did not go above 8° C. The reaction was stirred for 4 hours and then permitted to stand at ambient temperature for 16 hours. The reaction was poured into water and extracted with ethyl acetate. The ethyl acetate was washed (water), dried (MgSO4), and the solvent concentrated to afford 25.4 g of a reddish, dark oil. About 12.0 g of the oil was chromatographed an HPLC columns. Concentration of the largest fractions gave 5.4 g or 2-(3 chloropropoxy) aniline as an oil.

来源