反应详情

温度

120 °C

A mixture of 4-bromo-3-trifluoromethoxybenzonitrile (10.0 g, 37.6 mmol), K2CO3 (15.6 g, 113 mmol), trimethylboroxine (5.5 mL, 39.5 mmol) and DMF (150 mL) is degassed for 10 min with nitrogen before Pd(PPh3)4 (4.34 g, 3.76 mmol) is added. The mixture is then sealed and heated to 120° C. for 14 h. The mixture is then concentrated and then partitioned between Et2O and 50% brine solution. The aqueous phase is further extracted with Et2O and the combined organic layers are dried (Na2SO4) and concentrated. The residue is purified via flash chromatography (10% EtOAc/hexanes) to give 4-methyl-3-trifluoromethoxybenzonitrile. H NMR (400 MHz, CDCl3) δ (ppm) 2.40 (s, 3H), 7.40 (d, J=7.7 Hz, 1H), 7.50 (s, 1H), 7.51 (dd, J=7.7, 1.5 Hz, 1H). MS (ESI) m/z 202.1.

1. additionis added
2. customThe mixture is then sealed
3. concentrationThe mixture is then concentrated
4. custompartitioned between Et2O and 50% brine solution
5. extractionThe aqueous phase is further extracted with Et2O
6. dry with materialthe combined organic layers are dried (Na2SO4)
7. concentrationconcentrated
8. customThe residue is purified via flash chromatography (10% EtOAc/hexanes)