Benzyl Bromide → 3-(Benzyloxy)-2-chloropyridine

HRID 1809639Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1809639
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(C)=O>[CH2:16]([O:8][C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][CH:6]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 811362-Chloro-3-pyridinol

Produkt 1

HCID 8193743-(Benzyloxy)-2-chloropyridineAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 2-chloropyridin-3-ol (16.3 g, 125 mmol) and K2CO3 (24.3 g, 176 mmol) in acetone (150 ml) was added dropwise (bromomethyl)benzene (17.9 ml, 151 mmol). The mixture was stirred overnight at 50° C. and then concentrated to dryness. Water (100 ml) was added and the mixture extracted with CH2Cl2. The organics were dried over Na2SO4, and concentrated to a crude residue that was dissolved in 20 ml CH2Cl2. Et2O (250 ml) was added and then the solvent was decanted from the residue. The residue was then purified on a silica gel plug by eluting with 25% EtOAc/Hexanes to give 3-(benzyloxy)-2-chloropyridine (22.3 g, 80% yield) as a solid.

Aufarbeitung

  1. concentrationconcentrated to dryness
  2. additionWater (100 ml) was added
  3. extractionthe mixture extracted with CH2Cl2
  4. dry with materialThe organics were dried over Na2SO4
  5. concentrationconcentrated to a crude residue that
  6. dissolutionwas dissolved in 20 ml CH2Cl2
  7. additionEt2O (250 ml) was added
  8. customthe solvent was decanted from the residue
  9. customThe residue was then purified on a silica gel plug
  10. washby eluting with 25% EtOAc/Hexanes

Quellen und Nachweise

ORD-Eintrag
ord-b11c1bedc03e4aeeb5f9d294ab4ef46b
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362037B2

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