Hydrochloric Acid → 4-Octyloxybiphenyl-4'-yl boronic acid

HRID 1243251

Reaktionsgleichung

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[B:23](OC)([O:26]C)[O:24]C.Cl>CCCCCC.C1COCC1>[CH2:15]([O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([B:23]([OH:26])[OH:24])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

A solution of n-butylithium (50.97 cm3, 0.1274 mol, 2.5M in hexane) was added dropwise to a cooled (−78° C.) stirred solution of 4-bromo-4′-octyloxybiphenyl (40.00 g, 0.1108 mol) in THF (400 cm3). After 1 h, trimethyl borate (23.05 g, 0.2216 mol) was added dropwise to the reaction mixture maintaining a temperature of −78° C. The reaction mixture was allowed to warm to room temperature overnight. 20% hydrochloric acid (350 cm3) was added and the resultant mixture stirred for 1 h. The product was extracted into diethyl ether (3×300 cm3). The combined organic layers were washed with water (300 cm3), dried (MgSO4), filtered and the filtrate evaporated down under partially reduced pressure. The crude product was stirred with hexane for 30 minutes and filtered off to yield a white powder (26.20 g, 73%, m.pt. 134–136° C.).

Aufarbeitung

temperaturemaintaining a temperature of −78° C
temperatureto warm to room temperature overnight
extractionThe product was extracted into diethyl ether (3×300 cm3)
washThe combined organic layers were washed with water (300 cm3)
dry with materialdried (MgSO4)
filtrationfiltered
customthe filtrate evaporated down under partially reduced pressure
filtrationfiltered off

Quellen und Nachweise

ORD-Eintrag: ord-f3ac16df9fed435fac7e859d0dfe5baa
Quelldatensatz: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07118787B2

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