تفاعل #710492

معادلة التفاعل

ammonia

triflic anhydride

2-(3,5-dichloropyridin-2-yl)-2,2-difluoroethanol

pyridine

→

2-(3,5-dichloropyridin-2-yl)-2,2-difluoroethanamine

المذيبات

brine

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwhile maintaining the temperature below 8° C
2. 2
   workup.ADDITIONwere added
3. 3
   استخلاصthe product extracted three times with 25 mL of ethyl acetate
4. 4
   أخرىThe organic phases were collected
5. 5
   غسيلwashed three times with 40 mL of brine
6. 6
   تجفيفdried over magnesium sulfate
7. 7
   أخرىAfater evaporation of the solvent under vacuum 1.09 g of brown oil
8. 8
   أخرىwere obtained
9. 9
   أخرىAfter purification by column chromatography on silica gel (heptane/ethyl acetate gradient) 0.65 g (50%) of 2-(3,5-dichloropyridin-2-yl)-2,2-difluoroethanamine (IIa-15)
10. 10
    أخرىwere obtained as a yellow oil, (M+1)=227, 19F-NMR (235 MHz, CDCl3) δ (ppm): −104.80 (CF2)

الإجراء التجريبي

To a solution of 1.3 g (5.7 mmol) of 2-(3,5-dichloropyridin-2-yl)-2,2-difluoroethanol (Int-9) in dry acetonitrile under argon, were added 0.744 mL (9.12 mmol) of dry pyridine. The reaction mixture was cooled to 0° C. and 1.06 mL (6.27 mmol) of triflic anhydride were added dropwise in 15 min while maintaining the temperature below 8° C. The reaction mixture was stirred at 0° C. for additional 30 min 9.9 mL of a 28% w/w aqueous solution of ammonia (144 mmol) were added and the reaction mixture was stirred at room temperature for 2 days. The reaction mixture was diluted with 50 mL of brine and the product extracted three times with 25 mL of ethyl acetate. The organic phases were collected, washed three times with 40 mL of brine and dried over magnesium sulfate. Afater evaporation of the solvent under vacuum 1.09 g of brown oil were obtained. After purification by column chromatography on silica gel (heptane/ethyl acetate gradient) 0.65 g (50%) of 2-(3,5-dichloropyridin-2-yl)-2,2-difluoroethanamine (IIa-15) were obtained as a yellow oil, (M+1)=227, 19F-NMR (235 MHz, CDCl3) δ (ppm): −104.80 (CF2).

المصدر