反应 #156293

反应方程式

hydrochloric acid

tert-butyl 3-oxobutanoate

magnesium chloride

4-bromo-2-nitrobenzoyl chloride

→

tert-butyl 2-(4-bromo-2-nitrobenzoyl)-3 -oxobutanoate

收率 64.0%

溶剂

ethyl acetate

water

tetrahydrofuran

tetrahydrofuran

pyridine

反应条件

后处理

1. 1
   温度warming to room temperature
2. 2
   workup.STIRRINGfurther stirring for 30 minutes
3. 3
   温度The mixture was cooled to −8° C.
4. 4
   workup.STIRRINGby stirring at the same temperature for 1 hour
5. 5
   温度warming to room temperature
6. 6
   workup.STIRRINGfurther stirring for 1.5 hours
7. 7
   其他The aqueous layer was separated
8. 8
   洗涤the organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine
9. 9
   干燥dried over anhydrous magnesium sulfate
10. 10
    其他The solvent was evaporated under reduced pressure

实验过程

Under a nitrogen atmosphere, to a suspension of 2.28 g of magnesium chloride in 50 mL of tetrahydrofuran was added 3.80 g of tert-butyl 3-oxobutanoate at room temperature. The mixture was cooled to −8° C., and 3.9 mL of pyridine was added thereto, followed by stirring at the same temperature for 30 minutes, warming to room temperature, and further stirring for 30 minutes. The mixture was cooled to −8° C., and a solution of 5.3 g of 4-bromo-2-nitrobenzoyl chloride in 20 mL of tetrahydrofuran was added thereto, followed by stirring at the same temperature for 1 hour, warming to room temperature, and further stirring for 1.5 hours. The mixture was poured into a mixture of water and ethyl acetate, and adjusted to pH 3 with concentrated hydrochloric acid. The aqueous layer was separated, and then the organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 4.95 g of tert-butyl 2-(4-bromo-2-nitrobenzoyl)-3 -oxobutanoate.

来源