Hydrochloric Acid → 4'-Pentyloxybiphenyl-4-boronic Acid

HRID 439700

Reaktionsgleichung

[CH2:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C([Li])CCC.C([O:28][B:29](OC(C)C)[O:30]C(C)C)(C)C.Cl>O1CCCC1>[CH2:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([B:29]([OH:30])[OH:28])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To a stirred suspension of 4-(4-n-pentoxyphenyl)bromobenzene (1.0 g, 3.13 mmol) in anhydrous tetrahydrofuran (20 ml) at -78° C. under a nitrogen atmosphere was added n-butyllithium in hexanes (2.5M, 1.32 ml, 3.30 mmol). After a period of 15 min, triisopropylborate (760 μl, 3.30 mmol) was added. Stirring at -78° C. was continued for 15 min and then at 25° C. for 40 min. The mixture was acidified with 0.5N HCl (20 mL) and then partitioned between ether (50 ml) and water (40 ml). The organic phase was washed with water (3×) and brine and dried with magnesium sulfate. The solvent was removed in vacuo to give 4-(4-n-pentoxyphenyl)phenylboronic acid (750 mg) as a white solid: 1H NMR (400 MHZ, DMSO-d6) δ 0.89 (t, 3, J=7.2 Hz), 1.38 (m, 4 ), 1.72 (m, 2), 3.99 (t, 2, J=6.5 Hz), 6.99 (d, 2, J=8.8 Hz), 7.57 (d, 2, J=8.2 Hz), 7.60 (d, 2, J=8.8 Hz), 7.83 (d, 2, J=8.2 Hz).

Aufarbeitung

waitwas continued for 15 min
waitat 25° C. for 40 min
custompartitioned between ether (50 ml) and water (40 ml)
washThe organic phase was washed with water (3×) and brine
dry with materialdried with magnesium sulfate
customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-29d1296b53a4438d9b7086e9a61b7440
Quelldatensatz: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05516756

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