Hydrochloric Acid → HCID 86642844, Verbindung

To a mixture of 0.348 g (1.13 mmole) of methanesulfonic acid 2-dimethoxymethyl-4-fluoro-5-nitro-phenyl ester (IV.46a) and 4 mL of dimethylsulfoxide, cooled briefly in an ice bath, was added dropwise a cold solution of 0.10 g of potassium hydroxide in 1 mL of dimethylsulfoxide-water (1:1). The resulting dark red mixture was stirred at room temperature for 15 minutes and then was made acidic by addition of 1 M hydrochloric acid to give a yellow mixture. The mixture was partitioned between 50 mL of ethyl acetate and 50 mL of water. The aqueous layer was extracted three times with 25 mL of ethyl acetate. The combined organic layers were washed three times with 30 mL of water, once with 30 mL of brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 0.195 g of 5-fluoro-2-hydroxy-4-nitro-benzaldehyde (IV.46b) as a yellow solid.

1. temperaturecooled briefly in an ice bath
2. customto give a yellow mixture
3. customThe mixture was partitioned between 50 mL of ethyl acetate and 50 mL of water
4. extractionThe aqueous layer was extracted three times with 25 mL of ethyl acetate
5. washThe combined organic layers were washed three times with 30 mL of water
6. dry with materialonce with 30 mL of brine, dried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-5ecc1b3529894e07b3a13d2a7373f954

Quelldatensatz

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08044213B2