p-Toluenesulfonic acid → 2-Bromo-5-(dimethoxymethyl)pyridine

HRID 885836Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 885836
[Br:1][C:2]1[N:7]=[CH:6][C:5](C=O)=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:21](OC)([O:24][CH3:25])[O:22][CH3:23].C([O-])(O)=O.[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:21]([O:24][CH3:25])[O:22][CH3:23])=[CH:6][N:7]=1

Komponenten

6

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 117692346-Bromo-3-pyridinecarboxaldehyde

Produkt 1

HCID 64252132-Bromo-5-(dimethoxymethyl)pyridineAusbeute 95,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 6-bromopyridine-3-carbaldehyde (3.07 g, 16.5 mmol), p-toluenesulfonic acid (386 mg, 2.02 mmol) and trimethyl orthoformate (1.97 ml, 18 mmol) in MeOH (80 ml) was stirred at room temperature for 48 hours. The mixture was then brought to basic conditions with a 5% NaHCO3 solution and extracted twice with diethyl ether. The pooled organic phases were dried over Na2SO4 and evaporated to dryness to give 3.66 g of 2-bromo-5-dimethoxymethyl-pyridine as a pale yellow oil.

Aufarbeitung

  1. extractionextracted twice with diethyl ether
  2. dry with materialThe pooled organic phases were dried over Na2SO4
  3. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-da5f42b359da4c28b399296303b378bb
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242175B2

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