反应详情

温度

0 °C

To a solution of 5-bromo-2-naphthoic acid (4.3 g, 17 mmol)) in dry pyridine (75 mL) at 0° C. was added methanesulfonyl chloride (1.4 mL, 18 mmol). After stirring at 0° C. for 1 h, ammonia gas was bubbled through the solution for 10 min, whilst maintaining the temperature below 5° C. During the gas addition the solution became viscous, so additional dry pyridine (˜30 mL) was added. Excess ammonia was removed in vacuo, the solution again cooled to 0° C., then treated with additional methanesulfonyl chloride (12.5 mL) and allowed to warm to room temperature overnight. The solution was poured onto ice cold water, the mixture stirred for 30 min and the brown precipitate collected by filtration, washed on the sinter with ice cold water, then dried in vacuo. The crude product was dissolved in hot chloroform (˜35 mL) and insoluble material filtered off. The chloroform was removed and the residue dissolved in a minimum volume of ether at reflux. Hexane was added until the solution remained turbid at reflux, the solution filtered rapidly into a pre-heated flask, and allowed to cool slowly to room temperature. The precipitate was collected by filtration, washed with hexane, and dried in vacuo, to yield 5-bromo-2-naphthonitrile. Further crops were obtained by cooling the filtrate at −18° C. overnight.

1. customammonia gas was bubbled through the solution for 10 min
2. temperaturewhilst maintaining the temperature below 5° C
3. additionDuring the gas addition the solution
4. additionso additional dry pyridine (˜30 mL) was added
5. customExcess ammonia was removed in vacuo
6. temperaturethe solution again cooled to 0° C.
7. additiontreated with additional methanesulfonyl chloride (12.5 mL)
8. temperatureto warm to room temperature overnight
9. additionThe solution was poured onto ice cold water
10. stirringthe mixture stirred for 30 min
11. filtrationthe brown precipitate collected by filtration
12. washwashed on the sinter with ice cold water
13. customdried in vacuo
14. dissolutionThe crude product was dissolved in hot chloroform (˜35 mL)
15. filtrationinsoluble material filtered off
16. customThe chloroform was removed
17. dissolutionthe residue dissolved in a minimum volume of ether
18. temperatureat reflux
19. additionHexane was added until the solution
20. temperatureat reflux
21. filtrationthe solution filtered rapidly into a pre-heated flask
22. temperatureto cool slowly to room temperature
23. filtrationThe precipitate was collected by filtration
24. washwashed with hexane
25. customdried in vacuo