反应详情

温度

85 °C

A mixture of 6-bromo-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one (1.5 g, 5.9 mmol), 3-chlorophenyl boronic acid (1.83 g, 11.7 mmol), tetrakis(triphenylphosphine)-palladium (0) (0.35 g, 0.3 mmol), and sodium carbonate (2.48 g, 23.4 mmol) in a mixture of DME and water (40 mL/10 mL) was degassed to remove the oxygen and then heated at 85° C. under a blanket of nitrogen for 3 hours. The reaction mixture was cooled to ambient temperature and quenched with a saturated aqueous ammonium chloride solution (20 mL). Ethyl acetate (50 mL) was added and the organic layer was separated. The aqueous layer was extracted with ethyl acetate (3×15 mL). The combined organic layers were washed with brine and dried with MgSO4. The solvent was removed in vacuo and the residue was purified by silica gel flash chromatography (hexane:ethyl acetate/2:1) to afford 6-(3-chlorophenyl)-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one as a yellowish solid (1.4 g, 82%): mp 158-159° C.; 1H-NMR (DMSO-d6) δ 10.31 (s, 1H, D2O exchangeable), 7.75 (s, 1H), 7.61 (m, 3H), 7.46 (t, 1H, J=7.9 Hz), 7.39 (dd, 1H, J=7.0, 1.1 Hz), 6.96 (d, 1H, J=8.6 Hz), 1.68 (s, 6H); Anal. Calcd. For C16H14ClNO2.0.1H2O: C, 66.37; H, 4.94; N, 4.84. Found: C, 66.14; H, 4.61; N, 4.71.

1. customwas degassed
2. customto remove the oxygen
3. temperatureThe reaction mixture was cooled to ambient temperature
4. customquenched with a saturated aqueous ammonium chloride solution (20 mL)
5. additionEthyl acetate (50 mL) was added
6. customthe organic layer was separated
7. extractionThe aqueous layer was extracted with ethyl acetate (3×15 mL)
8. washThe combined organic layers were washed with brine
9. dry with materialdried with MgSO4
10. customThe solvent was removed in vacuo
11. customthe residue was purified by silica gel flash chromatography (hexane:ethyl acetate/2:1)