Water → 4-Bromo-2,6-dimethylpyridine 1-oxide

HRID 2071156

Reaktionsgleichung

Reaktionsgleichung von HRID 2071156
[CH3:1][C:2]1[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=[C:4]([CH3:11])[N+:3]=1[O-:12].C([Br:16])(=O)C.O.C([O-])(O)=O.[Na+]>CCOC(C)=O.C(Cl)(Cl)Cl>[Br:16][C:6]1[CH:7]=[C:2]([CH3:1])[N+:3]([O-:12])=[C:4]([CH3:11])[CH:5]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 10482Acetyl bromideHCID 209452,6-Lutidine, 4-nitro-, 1-oxideHCID 516892Sodium Bicarbonate

Produkt 1

HCID 124930354-Bromo-2,6-dimethylpyridine 1-oxideAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of 2.4 g of 2,6-dimethyl-4-nitropyridine 1-oxide and 16.5 mL of acetyl bromide was stirred at 75° C. under a CaCl2 drying tube for 4 h. The mixture was added to ice with H2O, CHCl3, and EtOAc and solid NaHCO3 was added to pH=7-8. The aqueous layer was extracted with CHCl3 (3×), and the combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (1 to 5) % MeOH/CHCl3 provided 1.39 g of 4-bromo-2,6-dimethylpyridine 1-oxide as a pale brown solid in 48% yield.

Aufarbeitung

  1. additionwas added to pH=7-8
  2. extractionThe aqueous layer was extracted with CHCl3 (3×)
  3. dry with materialthe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash silica gel chromatography (1 to 5) % MeOH/CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-c1d60ff99e7a4063a9433b59ea76c1f4
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299267B2

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