Trimethyl borate → 4-Benzyloxy-2-(trifluoromethoxy)phenylboronic acid
Reaktionsgleichung
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[C:11]([O:16][C:17]([F:20])([F:19])[F:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.C[O:27][B:28](OC)[O:29]C>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([B:28]([OH:29])[OH:27])=[C:11]([O:16][C:17]([F:20])([F:19])[F:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
To a mixture of 4-(benzyloxy)-1-bromo-2-(trifluoromethoxy)benzene (1.8 g, 5.19 mmol) in THF (20 mL) was added butyllithium (2.5 M in THF, 2.28 mL, 5.70 mmol) at −78° C. dropwise over 10 minutes. The reaction mixture was stirred at −78° C. for 1 h, then trimethylborate (1.73 mL, 15.6 mmol) was added. The mixture was warmed to room temperature and stirred overnight. The mixture was concentrated from diethyl ether three times and the residue was dried on high vacuum to provide the title compound as a gummy solid (2.2 g, 61% pure, 83% yield). The crude material was carried on without further purification. MS (M−1)=311.3
Aufarbeitung
- temperatureThe mixture was warmed to room temperature
- stirringstirred overnight
- concentrationThe mixture was concentrated from diethyl ether three times
- customthe residue was dried on high vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-225159859b19461c93f562a0e1dbbd20
- Quelldatensatz
- uspto-grants-2014_05
- Patentnummer
- US08729263B2
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