Acetic Acid → 2-Chloro-6-(trifluoromethyl)pyridine-3-carbaldehyde

Temperature

-78 °C

2-Chloro-6-(trifluoromethyl)nicotinonitrile (1.0 g, 4.84 mmol) was diluted with toluene (5.0 mL), placed under nitrogen and cooled to −78° C. DIBAL-H (9.68 mL, 9.68 mmol) was added dropwise and the reaction was stirred for 1 hour. The reaction was warmed to 0° C. and acetic acid (2 mL in 8 mL of water) was added dropwise. After stirring for 2 hours, the reaction was extracted twice with ethyl acetate, washed with Rochelle's salt, dried over MgSO4, filtered and concentrated. The material was loaded onto silica gel and eluted with 5% ethyl acetate/hexanes to 30% ethyl acetate/hexanes to yield 2-chloro-6-(trifluoromethyl)nicotinaldehyde (337 mg, 1.61 mmol, 33.2% yield) as a clear oil.

1. temperatureThe reaction was warmed to 0° C.
2. stirringAfter stirring for 2 hours
3. extractionthe reaction was extracted twice with ethyl acetate
4. washwashed with Rochelle's salt
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. washeluted with 5% ethyl acetate/hexanes to 30% ethyl acetate/hexanes

ORD record

ord-b469cc8606ac4c20b0c79bbc82ec1d4c

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785445B2