Benzyl Alcohol → 6-(Benzyloxy)-2-bromo-3-chloropyridine

HRID 1521943Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1521943
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[Br:15][C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[C:18](F)[N:17]=1>O1CCCC1.C(OCC)(=O)C.O>[CH2:1]([O:8][C:18]1[N:17]=[C:16]([Br:15])[C:21]([Cl:22])=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 244Benzyl AlcoholHCID 23665647Potassium tert-butoxideHCID 754123402-Bromo-3-chloro-6-fluoropyridine

Produkt 1

HCID 904122516-(Benzyloxy)-2-bromo-3-chloropyridine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of benzyl alcohol (55.5 mg, 0.513 mmol) in tetrahydrofuran (5 mL) at 0° C. was added potassium tert-butoxide (57.6 mg, 0.513 mmol) and the mixture was stirred at 0° C. for 2 hours. The mixture was cooled to −78° C. and a solution of 2-bromo-3-chloro-6-fluoropyridine (120 mg, 0.570 mmol) in 2 mL tetrahydrofuran was added. After stirring at −78° C. for 1 hour the mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with water and brine, dried over sodium sulfate and concentrated. Purification by column chromatography (silica gel, 20% ethyl acetate in hexane) afforded the title compound. LCMS: 299.9 (M+3)+.

Aufarbeitung

  1. temperatureThe mixture was cooled to −78° C.
  2. stirringAfter stirring at −78° C. for 1 hour the mixture
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customPurification by column chromatography (silica gel, 20% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-9c22a9f1bb3846c297b3deb79a3df96e
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073922B2

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