Water → 2-Chloro-5-fluoro-4-hydroxybenzaldehyde

Temperatur

90 °C

To 2-chloro-4,5-difluoro-benzaldehyde (110, 0.40 g, 2.30 mmol, prepared as described in Example 37) in N,N-dimethylformamide (10.0 mL) were added 2-(2-methoxyethoxy)-ethanol, (0.327 g, 2.72 mmol) and cesium carbonate (0.886 g, 2.72 mmol). The reaction was stirred at 90° C. overnight. The reaction was poured into water, acidified to pH around 5, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 30% ethyl acetate in hexane to give a white solid (111, 0.24 g, 61.0%). MS (ESI) [M+H+]+=173.1.

1. extractionextracted with ethyl acetate
2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
3. filtrationfiltered
4. concentrationThe filtrate was concentrated
5. custompurified by silica gel column chromatography
6. washeluting with 30% ethyl acetate in hexane
7. customto give a white solid (111, 0.24 g, 61.0%)

ORD-Eintrag

ord-013b2d1d8f044bdf982b6428723deb1d

Quelldatensatz

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07872018B2