Phenol → HCID 89781951, Verbindung

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A mixture of 8-bromo-2-chloroquinazoline (Ark Pharm Inc, Libertyville Ill.; 0.550 g, 2.259 mmol), cesium carbonate (0.883 g, 2.71 mmol), and phenol (0.234 g, 2.485 mmol) in 3 mL DMSO was sealed and heated to 120° C. for 2 h. The reaction was then partitioned between water and EtOAc. The organic layer was sequentially washed with water (2×), and saturated aq. NaCl (1×), then dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The material was treated with DCM and purified by silica gel chromatography using 0-20% EtOAc/hexane. The material-containing fractions were concentrated to afford 8-bromo-2-phenoxyquinazoline (0.486 g, 1.614 mmol, 71% yield) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ ppm 9.25 (1H, s), 8.15 (1H, dd, J=7.6, 1.4 Hz), 7.87 (1H, dd, J=8.0, 1.4 Hz), 7.34-7.50 (5H, m), 7.26-7.31 (1H, m). m/z (ESI, +ve) 302.9 (M+H)+.

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