تفاعل #309727

معادلة التفاعل

CO2

BuLi

DIPEA

2-chloro-7-(trifluoromethyl)quinoline

→

2-chloro-7-(trifluoromethyl)quinoline-3-carboxylic acid

المردود 71.0%

المذيبات

THF

THF

THF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas carried out for a further 30 min at −78° C
3. 3
   workup.ADDITIONThe reaction solution was then poured
4. 4
   أخرىwas removed in vacuo
5. 5
   workup.ADDITIONwas then added
6. 6
   أخرىthe phases were separated
7. 7
   استخلاصextracted with EA
8. 8
   غسيلThe organic phase was washed with water and brine
9. 9
   تجفيفdried over Na2SO4
10. 10
    ترشيحfiltered
11. 11
    تركيزconcentrated in vacuo

الإجراء التجريبي

11 ml of BuLi (1M in hexane) were added dropwise at −78° C. to a solution of 1.9 ml (11 mmol) of DIPEA in THF (77 ml). After stirring for 30 min at −78° C., a solution of 2.31 g (10 mmol) of 2-chloro-7-(trifluoromethyl)quinoline in THF (30 ml) was added and stirring was carried out for a further 30 min at −78° C. The reaction solution was then poured onto finely divided, solid CO2. After heating to RT, most of the THF was removed in vacuo. A 1M aq. NaOH soln. was then added and the phases were separated. The aqueous phase was acidified with 10% hydrochloric acid and extracted with EA. The organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. There were obtained as residue 2.12 g (7.7 mmol, 71%) of 2-chloro-7-(trifluoromethyl)quinoline-3-carboxylic acid, which was reacted further without additional purification.

المصدر