تفاعل #719538

معادلة التفاعل

2,2,3,3,3-pentafluoro-1-propanol

5-Bromo-6-chloro-2-pyridinecarboxylic acid

potassium tert-butoxide

DMF

→

title compound

المردود 20.0%

5-Bromo-6-(2,2,3,3,3-pentafluoro-propoxy)-pyridine-2-carboxylic acid

المردود 20.0%

المذيبات

THF

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   أخرىto give a yellow suspension
2. 2
   درجة الحرارةAfter cooling the mixture
3. 3
   workup.ADDITIONwas poured
4. 4
   غسيلthe combined mixture was washed with cold 1 M HCl (1×10 mL)
5. 5
   استخلاصThe aqueous layer was extracted with ethyl acetate (50 mL)
6. 6
   تجفيفdried with Na2SO4
7. 7
   تركيزconcentrated in vacuo
8. 8
   أخرىThe residue was purified by chromatography (silica gel, 20 g, 0% to 100% ethyl acetate in heptane)
9. 9
   أخرىfurther purified by preparative HPLC

الإجراء التجريبي

5-Bromo-6-chloro-2-pyridinecarboxylic acid (CAN 959958-25-9; 0.6 g, 2.54 mmol) and potassium tert-butoxide (712 mg, 6.34 mmol) were combined with DMF (30 mL) and THF (10 mL) to give a yellow suspension. To this suspension was added 2,2,3,3,3-pentafluoro-1-propanol (CAN 422-05-9; 3.01 g, 2 ml, 20.1 mmol) and the mixture was heated to 140° C. for 20 hours. After cooling the mixture was poured was poured into ethyl acetate (75 mL) and the combined mixture was washed with cold 1 M HCl (1×10 mL). The aqueous layer was extracted with ethyl acetate (50 mL). The organic layers were combined, dried with Na2SO4 and concentrated in vacuo. The residue was purified by chromatography (silica gel, 20 g, 0% to 100% ethyl acetate in heptane) and further purified by preparative HPLC to give the title compound (0.176 g 20%) as off white solid; MS (EI) 350.1 (M+H)+.

المصدر