反应详情

温度

90 °C

The 3-bromoquinoline (300 g, 1.44 mmol), ethyl acrylate (168 g, 1.68 mmol), palladium(II) acetate (32.3 g, 144 mmol), tetrabutylammonium bromide (478 g 1.44 mol), and sodium bicarbonate (483.9 g, 5.76 mol) were combined in a 5-L round-bottom flask with overhead stirring and 3 L dimethyl formamide (anhydrous). The reaction mixture was heated to 90° C. with heating mantle. After 30 minutes, 3-bromoquinoline was not detected by HPLC. The reaction was cooled to room temperature with an ice bath, and 2.65 L of ethyl acetate was added. The organic layer was washed with 1500 mL H2O. The aqueous layer was extracted with 4×1 L of 1:1 toluene/ethyl acetate; the combined organic layers were then washed with 6×1 L brine, then evaporated to give 217.4 g (65% of desired product).

1. temperaturewith heating mantle
2. temperatureThe reaction was cooled to room temperature with an ice bath
3. washThe organic layer was washed with 1500 mL H2O
4. extractionThe aqueous layer was extracted with 4×1 L of 1:1 toluene/ethyl acetate
5. washthe combined organic layers were then washed with 6×1 L brine
6. customevaporated