Benzyl Bromide → 2-(Benzyloxy)-4-bromopyridine

HRID 71724

Reaktionsgleichung

Reaktionsgleichung von HRID 71724
[Br:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[CH2:9]([O:8][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][N:5]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

5

Edukt 2

HCID 7498Benzyl BromideHCID 8171154-Bromo-2-hydroxypyridine

Produkt 1

HCID 532173892-(Benzyloxy)-4-bromopyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418647HCID 178418647, VerbindungKatalysatorHCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 4-Bromo-1H-pyridin-2-one (0.613 g), silver carbonate (0.63 g) and benzyl bromide (0.50 mL) in benzene (10 mL) was heated at 50° C. for 24 hours, protected from light. Reaction mixture stirred ambient temperature for 16 hours. Reaction mixture was filtered through a pad of CELITE, which was washed ethyl acetate. The filtrate was concentrated and purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes) to give 2-Benzyloxy-4-bromo-pyridine (0.6043 g): LCMS-ESI+: calc'd for C12H11BrNO: 265.12 (M+H+). Found: 263.8, 265.8 (M+H+).

Aufarbeitung

  1. customReaction mixture
  2. customReaction mixture
  3. filtrationwas filtered through a pad of CELITE, which
  4. washwas washed ethyl acetate
  5. concentrationThe filtrate was concentrated
  6. custompurified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b18655ce0d4f456aa6bcc15e60d2d09f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822430B2

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