Hydrochloric Acid → 3,5-Dimethylbiphenyl-4-ylboronic acid
Reaktionsgleichung
C([Li])(C)(C)C.[CH3:6][C:7]1[CH:8]=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]=[C:11]([CH3:13])[CH:12]=1.C[O:21][B:22](OC)[O:23]C.Cl>O1CCCC1>[CH3:10][CH2:9][CH2:8][CH:7]([CH3:12])[CH3:6].[CH3:6][C:7]1[C:12]([B:22]([OH:23])[OH:21])=[C:11]([CH3:13])[CH:10]=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=1Komponenten
Edukt 4
Produkt 2
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
tert-Butyllithium (1.7 M solution in hexane, 36.2 ml, 61.6 mmol) is added dropwise to a solution of 3,5-dimethylbiphenyl (7.27 g, 28 mmol) in dry tetrahydrofuran (150 ml) at −78° C. under an atmosphere of nitrogen. The reaction mixture is stirred at −78° C. for 30 minutes, then trimethylborate (9.54 ml, 84 mmol) is added. The resulting mixture is stirred at −78° C. for 30 minutes and then allowed to warm to room temperature. The reaction mixture is acidified with 10% aqueous hydrochloric acid solution and extracted with diethyl ether (2×150 ml). The organic layers are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure to give a yellow solid. Trituration with isohexane gives 3,5-dimethylbiphen-4-ylboronic acid as a white powder (5.89 g).
Aufarbeitung
- stirringThe resulting mixture is stirred at −78° C. for 30 minutes
- temperatureto warm to room temperature
- extractionextracted with diethyl ether (2×150 ml)
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customthe filtrate is evaporated under reduced pressure
- customto give a yellow solid
Quellen und Nachweise
- ORD-Eintrag
- ord-9b668601273d45edbebdb6c48cea7c55
- Quelldatensatz
- uspto-grants-2014_11
- Patentnummer
- US08895761B2
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