Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 2-Bromo-5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridine

HRID 1881839Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881839
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([OH:11])[CH2:9][OH:10])=[CH:4][CH:3]=1.[C:12]1(C)[CH:17]=CC(S([O-])(=O)=O)=C[CH:13]=1.[NH+]1C=CC=CC=1>CC(C)=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][O:10][C:12]([CH3:17])([CH3:13])[O:11]2)=[CH:6][N:7]=1

Komponenten

5

Edukt 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 469414371-(6-Bromopyridin-3-yl)ethane-1,2-diol

Produkt 1

HCID 469414392-Bromo-5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridineAusbeute 267,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1-(6-bromopyridin-3-yl)ethane-1,2-diol (4.20 g) in acetone (80 mL) was added pyridinium p-toluenesulfonate (1.50 g), and the mixture was stirred with heating under reflux for 3 hr. The reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give the title compound (4.12 g, yield 72%) as a pale-yellow solid. MS: 260 (MH+).

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux for 3 hr
  3. washwashed with water
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-49800bb3df6444c399f4281ceabb8a12
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318746B2

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