Sulfuric Acid → Ethyl 2-(2-bromopyridin-4-yl)acetate

HRID 538330Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 538330
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:4][N:3]=1.S(=O)(=O)(O)O.C([O-])(O)=O.[Na+].[C:22](OCC)(=O)[CH3:23]>C(O)C>[CH2:22]([O:10][C:9](=[O:11])[CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Br:1])[CH:7]=1)[CH3:23]

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 29921601(2-Bromopyridin-4-yl)acetic acid

Produkt 1

HCID 23106708Ethyl 2-(2-bromopyridin-4-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of (2-bromo-pyridin-4-yl)-acetic acid (60.0 g, 277.7 mmol) in ethanol (600 ml), conc: sulfuric acid (5.0 ml) was added at rt and the reaction mixture was heated at 90° C. for 9 h. Reaction mixture was cooled to rt and concentrated under reduced pressure to remove solvent completely. The residue obtained was cooled to 0° C. and pH was adjusted to 8 using 10% aqueous NaHCO3 solution. The resultant contents were worked up with ethyl acetate by washing with water, brine and dried over anhy. Na2SO4. Organic layer was concentrated under reduced pressure to obtain crude compound. Column chromatography purification of the crude compound using 15% ethyl acetate in hexane as eluent furnished title compound as a brown oil. Yield: 65.0 g (88.5%). TLC (30% ethyl acetate in hexane) Rf=0.39; LCMS: RtH7=0.824 [M+1]+=243.8 and 245.8; HPLC RtH9=3.759 min (69%); 1H NMR (300 MHz, CDCl3): δ 8.32 (t, 1H), 7.43 (s, 1H), 7.21-7.15 (M, 1H), 4.18 (q, 2H), 1.27 (t, 3H).

Aufarbeitung

  1. customReaction mixture
  2. temperaturewas cooled to rt
  3. concentrationconcentrated under reduced pressure
  4. customto remove solvent completely
  5. customThe residue obtained
  6. temperaturewas cooled to 0° C.
  7. washby washing with water, brine
  8. customdried over anhy
  9. concentrationOrganic layer was concentrated under reduced pressure
  10. customto obtain crude compound
  11. customColumn chromatography purification of the crude compound

Quellen und Nachweise

ORD-Eintrag
ord-e203dae9a9c44fb881787e09c4eaa866
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865712B2

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