Boron tribromide → 4-(6-Hydroxy-4-methylquinazolin-2-yl)benzoic acid

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Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

To a solution of 4-(6-methoxy-4-methylquinazolin-2-yl)benzoic acid (180 mg, 0.612 mmol) in anhydrous DCM (10 mL) was added BBr3 (0.29 mL, 3.05 mmol, d=2.64 g/mL) dropwise at 0° C. The resulting mixture was stirred at 25° C. for 16 hours. The reaction mixture was quenched with H2O (30 mL), then extracted with DCM (20 mL×3). The combined organic layers were washed with brine (20 mL), dried over anhydrous Na2SO4, filtered and concentrated to give the crude product. The crude product was washed with MeOH (10 mL) to give Compound V-2 (130 mg, yield 76%). 1H NMR (DMSO-d6 400 MHz): δ 13.06 (brs, 1H), 10.46 (brs, 1H), 8.60 (d, J=8.4 Hz, 2H), 8.09 (d, J=8.4 Hz, 2H), 7.95 (d, J=9.2 Hz, 1H), 7.56 (dd, J=8.8, 2.4 Hz, 1H), 7.41 (d, J=2.4 Hz, 1H), 2.90 (s, 3H). MS (ESI): m/z 280.9 [M+H]+.

Aufarbeitung

customThe reaction mixture was quenched with H2O (30 mL)
extractionextracted with DCM (20 mL×3)
washThe combined organic layers were washed with brine (20 mL)
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-3e57ebe2bd5b49198456e458c1c40267
Quelldatensatz: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09364481B2

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