Phosphorus oxychloride → 3-(Benzyloxy)-5-bromo-2-chloropyridine

HRID 2307755

Reaktionsgleichung

Reaktionsgleichung von HRID 2307755
[CH2:1]([O:8][C:9]1[CH:10]=[N+:11]([O-])[CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:19]>>[CH2:1]([O:8][C:9]1[C:10]([Cl:19])=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 582134893-(benzyloxy)-5-bromopyridine N-oxide

Produkt 1

HCID 226075323-(Benzyloxy)-5-bromo-2-chloropyridineAusbeute 40 %

Versuchsvorschrift

A solution of 3-(benzyloxy)-5-bromopyridine N-oxide (2.0 g, 7.1 mmol) in POCl3 (20 mL) was stirred at 100° C. for 7 hours, cooled to room temperature, concentrated, treated with ethyl acetate (50 mL), washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 10% ethyl acetate/hexane to provide the desired product (1.0 g, 40%). MS (DCI/NH3) m/e 299 (M+H)+.

Aufarbeitung

  1. concentrationconcentrated
  2. additiontreated with ethyl acetate (50 mL)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 10% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-541a024c85cd4d3b81f065af2f5575d4
Quelldatensatz
uspto-grants-2004_12
Patentnummer
US06831175B2

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