تفاعل #2190291

معادلة التفاعل

Carbon dioxide

TMEDA

4-Fluoro-2,2-diphenyl-benzo[1,3]dioxole

n-butyl lithium

→

acid

المردود 60.0%

4-fluoro-2,2-diphenyl-benzo[1,3]dioxole-5-carboxylic acid

المردود 60.0%

المذيبات

water

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto warm to 0° C.
2. 2
   استخلاصThe reaction was extracted twice with ethyl acetate
3. 3
   استخلاصextracted twice with ethyl acetate
4. 4
   غسيلThe organic layer was washed with brine
5. 5
   تجفيفdried over sodium sulfate
6. 6
   ترشيحfiltered
7. 7
   أخرىThe solvent was evaporated
8. 8
   workup.STIRRINGstirred for 10 minutes
9. 9
   ترشيحthe product was filtered off

الإجراء التجريبي

4-Fluoro-2,2-diphenyl-benzo[1,3]dioxole (5.8 g, 20 mmol) were dissolved in THF (40 ml). The reaction was cooled to −78° C. under argon. TMEDA (2.9 ml, 20 mmol) was added followed by n-butyl lithium (12.5 ml, 1.6 N in hexane) dropwise. The reaction was stirred at −78° C. for 2 hours. Carbon dioxide (20 g) was added at that temperature. The reaction was allowed to warm to 0° C. and poured into water (80 ml). The reaction was extracted twice with ethyl acetate. The aqueous layer was neutralized with 1N aqueous HCl solution, extracted twice with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and filtered. The solvent was evaporated and the residue suspended in n-hexane, stirred for 10 minutes and the product was filtered off to yield the acid as a white solid (4.0 g, 60%). m.p.: 189-191° C.

المصدر