反应详情

To a solution of 2-bromothiazole (0.26 g, 1.6 mmol) and 4-formylphenylboronic acid (0.48 g, 3.2 mmol) in toluene (16 mL) was added tetrakis(triphenylphosphine)palladium(0) (0.09 g, 0.08 mmol) and K2CO3 (0.33 g, 2.4 mmol) and the solution stirred at reflux for 16 h. The reaction was cooled to room temperature, diluted with water (50 mL) and ethyl acetate (50 mL). The organic layer was separated, washed with brine (30 mL), dried (MgSO4), filtered, concentrated and purified by column chromatography on silica gel (2% MeOH/CH2Cl2) to give 4-(2-thiazolyl)-benzaldehyde (45 mg, 15%). 1H NMR (CDCl3) δ 7.45 (d, 1H, J=3.0 Hz), 7.90 (d, 1H, J=3.0 Hz), 7.97 (d, 2H, J=7.8 Hz), 8.15 (d, 2H, J=7.2 Hz), 10.07 (s, 1H (CHO)).

1. temperatureat reflux for 16 h
2. customThe organic layer was separated
3. washwashed with brine (30 mL)
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated
7. custompurified by column chromatography on silica gel (2% MeOH/CH2Cl2)