Hydrochloric Acid → (4-Methoxy-2-{[(triisopropylsilyl)oxy]methyl}phenyl)boronic acid
Reaktionsgleichung
Br[C:2]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:3]=1[CH2:4][O:5][Si:6]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:12])[CH3:11])[CH:7]([CH3:9])[CH3:8].[Li]CCCC.[B:27](OC(C)C)([O:32]C(C)C)[O:28]C(C)C.Cl>C1COCC1>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:2]([B:27]([OH:32])[OH:28])=[C:3]([CH2:4][O:5][Si:6]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:12])[CH3:11])[CH:7]([CH3:9])[CH3:8])[CH:16]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
[(2-bromo-5-methoxybenzyl)oxy](triisopropyl)silane (1 eq.) was dissolved in anhydrous THF (0.43M solution) and the solution was cooled to −78° C. A solution of n-BuLi (1.6M in hexanes, 1.05 eq.) was added and the resulting mixture was left stirring for 1 h at −78° C. Then triisopropyl borate (50% in THF, 1.3 eq.) was added dropwise and the mixture was allowed to warm to RT overnight. 1N HCl was added and the resulting mixture was left stirring at RT for 30 min. THF was removed in vacuo and replaced with Et2O. The organic phase was washed with water and with brine, then dried over Na2SO4 and evaporated in vacuo. The product was obtained as a colorless oil (64% yield, 65% pure) which was used without further purification in the next reaction.
Aufarbeitung
- waitthe resulting mixture was left
- temperatureto warm to RT overnight
- waitthe resulting mixture was left
- stirringstirring at RT for 30 min
- customTHF was removed in vacuo
- washThe organic phase was washed with water and with brine
- dry with materialdried over Na2SO4
- customevaporated in vacuo
- customThe product was obtained as a colorless oil (64% yield, 65% pure) which
- customwas used without further purification in the next reaction
Quellen und Nachweise
- ORD-Eintrag
- ord-6bd34ecbd1284eb5b8f2f0048d99f7dc
- Quelldatensatz
- uspto-grants-2012_07
- Patentnummer
- US08232390B2
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