Citric Acid → 2-(Difluoromethyl)-3-fluoropyridine-4-carboxylic acid

HRID 1426287Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1426287
[F:1][CH:2]([F:14])[C:3]1[C:4]([F:13])=[C:5]([CH:10]=[CH:11][N:12]=1)[C:6]([O:8]C)=[O:7].O.[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.O>[F:14][CH:2]([F:1])[C:3]1[C:4]([F:13])=[C:5]([CH:10]=[CH:11][N:12]=1)[C:6]([OH:8])=[O:7]

Komponenten

6

Edukt 3

HCID 311Citric AcidHCID 168937Lithium hydroxide, monohydrateHCID 696732014-Pyridinecarboxylic acid, 2-(difluoromethyl)-3-fluoro-, methyl ester

Produkt 1

HCID 696736882-(Difluoromethyl)-3-fluoropyridine-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-(difluoromethyl)-3-fluoroisonicotinate (0.44 g, 2.1 mmol, from Step 4) in tetrahydrofuran (10 mL) was added a solution of lithium hydroxide monohydrate (0.45 g, 11 mmol) in water (10 mL). The reaction was stirred for 2 hours. The reaction mixture was acidified by the addition of a solution of citric acid. The product was extracted with three portions of DCM. The combined extracts were dried over sodium sulfate, decanted and concentrated to afford product, which was used without further purification in Step 6. H NMR (300 MHz, CD3OD): δ 8.57 (d, 1H), 7.99 (dd, 1H), 6.96 (t, 1H).

Aufarbeitung

  1. extractionThe product was extracted with three portions of DCM
  2. dry with materialThe combined extracts were dried over sodium sulfate
  3. customdecanted
  4. concentrationconcentrated
  5. customto afford product, which
  6. customwas used without further purification in Step 6

Quellen und Nachweise

ORD-Eintrag
ord-7a501e3dcb0c45dc98022dcd473e5a34
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933085B2

Notizen zur Reaktion

Wird geladen…