Lithium hydroxide, monohydrate → 6-Bromo-3-methoxypicolinic acid

HRID 2201525Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2201525
[Br:1][C:2]1[N:7]=[C:6]([C:8]([O:10]C)=[O:9])[C:5]([O:12][CH3:13])=[CH:4][CH:3]=1.O[Li].O>O1CCOCC1.O>[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[C:5]([O:12][CH3:13])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 70700803Methyl 6-bromo-3-methoxypicolinate

Produkt 1

HCID 714639656-Bromo-3-methoxypicolinic acidAusbeute 74,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

A solution of methyl 6-bromo-3-methoxypicolinate (3.0 g, 12.19 mmol) and LiOH.H2O (1.4 g, 33.36 mmol) in 1,4-dioxane/H2O (15 mL/15 mL) was stirred at RT overnight. The mixture was filtered and the filtrate was adjusted to pH=3 by aqueous HCl (2 M) and extracted with EtOAc. The combined organic phase was washed with brine, dried over Na2SO4 and concentrated to give the crude product of 6-bromo-3-methoxypicolinic acid (2.1 g, yield: 73%) without further purification. 1H-NMR (CDCl3, 400 MHz) δ 10.05 (br s, 1H), 7.70 (d, J=8.8 Hz, 1H), 7.40 (d, J=8.8 Hz, 1H), 4.01 (s, 3H). MS (M+H)+: 232/234.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. extractionextracted with EtOAc
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-953f57a4cf174d61b92d1ad6e008bd8d
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09364482B2

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