反应 #74390

反应方程式

(4S)-2-bromobicyclo[2.2.1]heptane-1-carboxylic acid

→

bicyclo[2.2.1]heptane-1-carboxylic acid

收率 81.3%

溶剂

acetic acid

acetic acid

反应条件

后处理

1. 1
   其他A 2-L reactor equipped with an overhead mechanical stirrer, condenser, nitrogen gas inlet port, temperature probe and reagent
2. 2
   workup.ADDITIONwas then added
3. 3
   洗涤to rinse the walls of the reactor
4. 4
   温度a gentle reflux (ca. 30 min)
5. 5
   温度The cooled
6. 6
   其他(room temperature) reaction mixture
7. 7
   洗涤was washed with acetic acid (1 (300 mL) and ethyl acetate (1 (500 mL)
8. 8
   浓缩The filtrate was concentrated
9. 9
   workup.ADDITIONwater (300 mL) was added
10. 10
    其他precipitation
11. 11
    过滤The precipitate was collected by filtration
12. 12
    洗涤washed with water
13. 13
    其他dried under vacuum at 35° C. overnight
14. 14
    workup.ADDITIONPentane (50 mL) was then added
15. 15
    workup.STIRRINGthe mixture was stirred vigorously for 20 min during which time a fine white precipitate
16. 16
    其他formed
17. 17
    过滤The resulting precipitate was filtered
18. 18
    洗涤washed with pentane (20 mL), and air
19. 19
    其他dried

实验过程

A 2-L reactor equipped with an overhead mechanical stirrer, condenser, nitrogen gas inlet port, temperature probe and reagent charging port, was placed under an atmosphere of nitrogen. The reactor was charged with zinc powder (<10 micron) (298 g, 4560 mmol) and acetic acid (500 mL). While vigorously stirring the heterogeneous mixture, (4S)-2-bromobicyclo[2.2.1]heptane-1-carboxylic acid (100 g, 456 mmol) was then added. A second portion of acetic acid (500 mL) was then used to rinse the walls of the reactor. The reaction mixture was brought to a gentle reflux (ca. 30 min) and then held at this temperature for 5 h. The cooled (room temperature) reaction mixture was passed through a pad of Celite, which was washed with acetic acid (1 (300 mL) and ethyl acetate (1 (500 mL). The filtrate was concentrated, water (300 mL) was added, and then the mixture was stirred vigorously to induce precipitation. The precipitate was collected by filtration, washed with water, and dried under vacuum at 35° C. overnight. Pentane (50 mL) was then added, and the mixture was stirred vigorously for 20 min during which time a fine white precipitate formed. The resulting precipitate was filtered, washed with pentane (20 mL), and air dried to afford bicyclo[2.2.1]heptane-1-carboxylic acid (52 g) as a white solid.

来源