p-Fluoronitrobenzene → 4,4,5,5-Tetramethyl-2-(2-(4-nitrophenoxy)phenyl)-1,3,2-dioxaborolane
Reaktionsgleichung
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])[O:3]1.C(=O)([O-])[O-].[K+].[K+].F[C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1>CN(C=O)C>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:16])([CH3:1])[O:3][B:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[O:5]1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 120 °C
Versuchsvorschrift
To a solution of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (2.00 g, 9.09 mmol) in DMF was added potassium carbonate (2.51 g, 18.2 mmol) and 1-fluoro-4-nitrobenzene (0.964 ml, 9.09 mmol). The reaction mixture was flushed with nitrogen, sealed, and heated to 120° C. After 18 h, water was added and the mixture was extracted 2× with EtOAc. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo, and the crude was purify by silica gel chromatography, eluting with 0-15% EtOAc/hexanes to give 4,4,5,5-tetramethyl-2-(2-(4-nitrophenoxy)phenyl)-1,3,2-dioxaborolane as a white solid. MS m/z=342 [M+1]+. Calc'd for C18H20BNO5: 341.17.
Aufarbeitung
- customThe reaction mixture was flushed with nitrogen
- customsealed
- additionwater was added
- extractionthe mixture was extracted 2× with EtOAc
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customthe crude was purify by silica gel chromatography
- washeluting with 0-15% EtOAc/hexanes
Quellen und Nachweise
- ORD-Eintrag
- ord-1097570c071b467f84cb122c5a581ec6
- Quelldatensatz
- uspto-grants-2009_07
- Patentnummer
- US07560551B2
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