Potassium Fluoride → 5-Chloro-2-(trifluoromethyl)pyridine

Temperature

60 °C

Into a 10-mL sealed tube purged and maintained with an inert atmosphere of nitrogen, was placed a solution of KF (53 mg, 0.91 mmol, 1.10 equiv) in NMP (3 mL), CuI (175 mg, 0.92 mmol, 1.10 equiv), trimethyl(trifluoromethyl)silane (119 mg, 0.84 mmol, 1.00 equiv) and 5-chloro-2-iodopyridine (as prepared in the previous step, 200 mg, 0.84 mmol, 1.00 equiv). The reaction mixture was stirred overnight at 60° C. The reaction was then quenched by the addition of 20 mL of ammonia (12%). The resulting solution was extracted with 2×20 mL of ethyl acetate. The combined organic layers were washed with 50 ml of brine, dried (Na2SO4), and concentrated to yield 5-chloro-2-(trifluoromethyl)pyridine as a yellow oil.

1. customInto a 10-mL sealed tube
2. custompurged
3. temperaturemaintained with an inert atmosphere of nitrogen
4. customas prepared in the previous step, 200 mg, 0.84 mmol, 1.00 equiv)
5. customThe reaction was then quenched by the addition of 20 mL of ammonia (12%)
6. extractionThe resulting solution was extracted with 2×20 mL of ethyl acetate
7. washThe combined organic layers were washed with 50 ml of brine
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated

ORD record

ord-00192ec116814752a7b0238403ba1fb0

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436023B2