Sodium Hydroxide → 6-Fluoro-4-methoxy-biphenyl-3-carboxylic acid

HRID 457978Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 457978
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]([F:13])=[CH:9][C:10]=1[O:11][CH3:12])=[O:4].[OH-].[Na+]>O1CCOCC1>[F:13][C:8]1[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[C:10]([O:11][CH3:12])[CH:9]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 220934916-Fluoro-4-methoxy-biphenyl-3-carboxylic acid methyl ester

Produkt 1

HCID 184681996-Fluoro-4-methoxy-biphenyl-3-carboxylic acidAusbeute 97,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirring solution of 6-fluoro-4-methoxy-biphenyl-3-carboxylic acid methyl ester (0.5 g, 2.3 mmol) in dioxane (8 mL, 0.3 M) was added 2N NaOH (6.0 mL, 12 mmol). After one hour at room temperature, the reaction mixture was concentrated, and 2N HCl was added. The aqueous layer was diluted with ether. The organic layer was separated, dried over Na2SO41 filtered and concentrated to afford a 6-fluoro-4-methoxy-biphenyl-3-carboxylic acid (0.55 g, 96%) as a pale yellow powder: Rf 0.18 (5% methanol in dichloromethane); 1H NMR (CDCl3, 300 MHz) δ 8.35 (d, J=9.0 Hz, 1 H), 7.55–7.52 (m, 2 H), 7.48–7.38 (m, 3 H), 6.89 (d, J=11.7 Hz, 1H), 4.12 (s, 3H).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. addition2N HCl was added
  3. additionThe aqueous layer was diluted with ether
  4. customThe organic layer was separated
  5. customdried over Na2SO41
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b0c126bb088642e4bad0d0d0f62bb2cb
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07189749B2

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