Methanol → Methyl 2-(5-bromopyridin-3-yl)acetate

HRID 445767

Reaktionsgleichung

Reaktionsgleichung von HRID 445767
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[N:6][CH:7]=1.S(=O)(=O)(O)O.[CH3:17]O>>[CH3:17][O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 28025392-(5-Bromopyridin-3-yl)acetic acid

Produkt 1

HCID 23398394Methyl 2-(5-bromopyridin-3-yl)acetate

Versuchsvorschrift

A mixture of (5-bromo-pyridin-3-yl)-acetic acid (ABCR, Karlsruhe, Germany, 4.54 mmol) and concentrated sulfuric acid (0.02 ml) in MeOH was refluxed for 13.5 h. The RM was concentrated, taken in EtOAc and sonicated. The organic layer was washed with saturated aqueous NaHCO3, with brine, dried over Na2SO4, filtered and evaporated to dryness to give the title compound as a brown oil. (HPLC: tR 2.21 min (Method A); M+H=230, 232 MS-ES)

Aufarbeitung

  1. temperaturewas refluxed for 13.5 h
  2. concentrationThe RM was concentrated
  3. customsonicated
  4. washThe organic layer was washed with saturated aqueous NaHCO3, with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-f336233cdd9e4e0db0c80e3722d06f41
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476294B2

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