反应详情

A mixture of commercial available 4-(hexyloxy)phenylboronic acid (25, 5.55 g, 25.0 mmol), 4-bromothiophene-2-carbaldehyde (5.25 g, 27.5 mmol), tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.13 mmol), toluene (25 mL), ethanol (15 mL) and aqueous sodium carbonate (2 M, 25 mL) was stirred under reflux for 18 hours under a nitrogen atmosphere. The reaction mixture was cooled to ambient temperature and the aqueous layer was extracted with dichloromethane (3×50 mL). The combined organic layers were washed with saturated sodium chloride (50 mL), and dried over magnesium sulfate. After filtration and concentration, the crude material was purified by recrystallization from ethyl acetate/petroleum ether (1/2, v/v) to afford the compound 1026 (3.8 g).

1. temperatureunder reflux for 18 hours under a nitrogen atmosphere
2. extractionthe aqueous layer was extracted with dichloromethane (3×50 mL)
3. washThe combined organic layers were washed with saturated sodium chloride (50 mL)
4. dry with materialdried over magnesium sulfate
5. filtrationAfter filtration and concentration
6. customthe crude material was purified by recrystallization from ethyl acetate/petroleum ether (1/2