Water → alpha-(2,3-Dichloro-4-methoxyphenyl)-2-pyridinemethanol

HRID 568641

Reaktionsgleichung

Reaktionsgleichung von HRID 568641
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[Cl:13][C:14]1[C:21]([Cl:22])=[C:20]([O:23][CH3:24])[CH:19]=[CH:18][C:15]=1[CH:16]=[O:17].O>C1COCC1>[Cl:13][C:14]1[C:21]([Cl:22])=[C:20]([O:23][CH3:24])[CH:19]=[CH:18][C:15]=1[CH:16]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)[OH:17]

Komponenten

6

Edukt 4

HCID 962WaterHCID 79732-BromopyridineHCID 130156892,3-Dichloro-4-methoxybenzaldehydeHCID 178418339Butyllithium

Produkt 1

HCID 13015690alpha-(2,3-Dichloro-4-methoxyphenyl)-2-pyridinemethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-65 °C

Versuchsvorschrift

29.3 g of 2-bromopyridine in 150 ml of dry THF is added to 75 ml of 2.6M n-butyllithium that was chilled to -65° C. 2,3-dichloro-4-methoxybenzaldehyde (38.0 g) is then added in 300 ml of THF and the reaction mixture allowed to come to room temperature. It is poured into H2O and the crystalline product filtered off, washed with ether and dried to give α-(2,3-dichloro-4-methoxyphenyl)-2-pyridinemethanol, mp 174°-176° C.

Aufarbeitung

  1. customto come to room temperature
  2. filtrationthe crystalline product filtered off
  3. washwashed with ether
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-386848d5c489420ea7ebd52b0c9b35f7
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04728662

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