Ethylamine → 3-Chloro-2-fluorobenzoic acid
Reaktionsgleichung
[Cl:1][C:2]1[C:3]([F:15])=[C:4]([C:8]([Si:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH2:16]([NH2:18])[CH3:17]>>[Cl:1][C:2]1[C:3]([F:15])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[Cl:1][C:2]1[C:3]([F:15])=[C:4]([C:8]([Si:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][CH:10]=1)[C:5]([NH:18][CH2:16][CH3:17])=[O:7]Komponenten
4
Versuchsvorschrift
The trimethylsilyl ester of 3-chloro-2-fluorobenzoic acid (11.66 g) was prepared in 84% yield using the method described in Example 207. This ester (2.47 g) was converted to 0.45 g of 3-chloro-2-fluoro-6-(trimethylsilyl)benzoic acid in 18% yield using the method of Example 207. The crude product was converted to the acid chloride by the procedure of example b. The acid chloride was reacted with 70% aq ethylamine using General Method E1 to afford the title compound. Purification by flash chromatography (ethyl acetate/hexanes) followed by recrystallization from pentane gave 84 mg of the title compound as an off-white solid (18%). m.p. 96°-97° C.
Quellen und Nachweise
- ORD-Eintrag
- ord-e57cc015a97c4297880c773a684cc44c
- Quelldatensatz
- uspto-grants-1998_01
- Patentnummer
- US05705513
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