2-Chlorobenzaldehyde → (2-Chloro-phenyl)-(2,4,6-trifluoro-pyridin-3-yl)-methanol

Temperatur

-78 °C

2,4,6-Trifluoropyridine (7.5 g, 56.36 mmol) was taken up in 9 mL of dry THF, and the reaction mixture was cooled to −78° C. under argon with stirring. Lithium diisopropylamine (42.3 mL of 2M solution in THF) was added dropwise, and the solution was stirred for 10 minutes. 2-Chlorobenzaldehyde (9.5 mL, 1.5 equiv) was added dropwise via syringe, and the reaction mixture was stirred for 15 minutes. The reaction was quenched by addition of saturated ammonium chloride and water, and the aqueous mixture was extracted once with EtOAc. The combined organic layers were washed with saturated brine and water, dried over MgSO4, filtered and evaporated. The residue was purified by FLASH column chromatography using 5%-10% EtOAc/Hexanes to yield 8.02 g of (2-Chloro-phenyl)-(2,4,6-trifluoro-pyridin-3-yl)-methanol. Mass spec., M+1=275.

1. stirringthe solution was stirred for 10 minutes
2. stirringthe reaction mixture was stirred for 15 minutes
3. customThe reaction was quenched by addition of saturated ammonium chloride and water
4. extractionthe aqueous mixture was extracted once with EtOAc
5. washThe combined organic layers were washed with saturated brine and water
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. customevaporated
9. customThe residue was purified by FLASH column chromatography

ORD-Eintrag

ord-23e439645cf94c81b92448b317f5dfca

Quelldatensatz

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07435731B2