Ammonium Chloride → (2,5-Dichloropyridin-3-yl)(2-fluoro-3-methoxy-6-vinylphenyl)methanol
Reaktionsgleichung
[Li]CCCC.Br[C:7]1[C:8]([Cl:14])=[N:9][CH:10]=[C:11]([Cl:13])[CH:12]=1.[F:15][C:16]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[C:20]([CH:26]=[CH2:27])[C:17]=1[CH:18]=[O:19].[NH4+].[Cl-]>C(OC(C)C)(C)C.C1C=CC=CC=1>[Cl:14][C:8]1[C:7]([CH:18]([C:17]2[C:20]([CH:26]=[CH2:27])=[CH:21][CH:22]=[C:23]([O:24][CH3:25])[C:16]=2[F:15])[OH:19])=[CH:12][C:11]([Cl:13])=[CH:10][N:9]=1Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
To a stirred solution of nBuLi (1.6 M in hexane, 29.0 mL, 46.4 mmol) in diisopropyl ether (80 mL) was added 3-bromo-2,5-dichloropyridine (10.5 g, 46.4 mmol) in diisopropylether (60 mL) slowly at −78° C. The resulting suspension was treated with 2-fluoro-3-methoxy-6-vinylbenzaldehyde (7.6 g, 42.2 mmol) in diisopropylether (60 mL) and benzene (3 mL), and allowed to stir at −78° C. for 30 min followed by warming to room temperature as the bath did. The mixture was treated with saturated NH4Cl solution and extracted with EtOAc (×3). The combined organics were washed with brine, dried (Na2SO4), concentrated, and purified by flash chromatography to afford the title compound.
Aufarbeitung
- temperatureby warming to room temperature as the bath
- extractionextracted with EtOAc (×3)
- washThe combined organics were washed with brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- custompurified by flash chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-006c1b9c4aad460b908701196ca4ad03
- Quelldatensatz
- uspto-grants-2009_06
- Patentnummer
- US07550478B2
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