تفاعل #62299

معادلة التفاعل

(6-bromo-2,3-difluorophenyl)trimethylsilane

N,N-diisopropylamine

N,N-dimethylformamide

→

title compound

5-Bromo-2,3-difluoro-4-trimethylsilanyl Benzaldehyde

المذيبات

tetrahydrofuran

water

ethyl acetate

tetrahydrofuran

hexane

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added at 0° C.
2. 2
   workup.ADDITIONwas added dropwise
3. 3
   workup.STIRRINGstirred at this temperature for 1 hour
4. 4
   درجة الحرارةto gradually warm to room temperature
5. 5
   workup.STIRRINGstirred fro 3 hours
6. 6
   غسيلthe organic layer was washed with saturated brine
7. 7
   تجفيفdried over anhydrous magnesium sulfate
8. 8
   أخرىthe solvent was evaporated
9. 9
   أخرىThe crude product was purified
10. 10
    أخرىseparated by silica gel column chromatography (n-hexane)

الإجراء التجريبي

Under nitrogen atmosphere, to a solution containing 6.34 mL of N,N-diisopropylamine in 100 mL of tetrahydrofuran, 26.4 mL of 1.57 Mn-butyllithium in hexane was added at 0° C., and stirred at this temperature for 10 minutes. After cooling to −78° C., a solution containing 10.0 g of (6-bromo-2,3-difluorophenyl)trimethylsilane in 100 mL of tetrahydrofuran was added dropwise, stirred at this temperature for 1 hour, then added dropwise with 2.92 mL of N,N-dimethylformamide, allowed to gradually warm to room temperature, and stirred fro 3 hours. After diluting with water and ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (n-hexane), to afford 9.70 g of the title compound as a colorless oil.

المصدر