反应详情

温度

85 °C

To a stirred degassed solution of 4-bromobenzaldehyde (371 mg, 2.00 mmol) and thiophene-2-boronic acid (287 mg, 2.24 mmol) in DME/THF (5 mL, 4:1) were added a 2 M Na2CO3 solution (3.0 mL) and Pd(PPh3)4 (110 mg, 0.095 mmol). The reaction mixture was flushed with argon and maintained under argon while being heated at 85° C. over 2 days. The mixture was then cooled and diluted with EtOAc (35 mL) and water (30 mL). The aqueous layer was washed with EtOAc (2×10 mL) and the combined organic extracts dried (Na2SO4), filtered and concentrated. Purification of the resultant oil by column chromatography on silica gel (Hexanes/EtOAc, 4:1) afforded the title compound (293 mg, 78%) as a yellow solid. 1H NMR (CDCl3) δ 7.14 (dd, 1H, J=5.1, 3.6 Hz), 7.40 (dd, 1H, J=5.1, 0.9 Hz), 7.46 (dd, 1H, J=3.6, 0.9 Hz), 7.76 (d, 2H, J=8.4 Hz), 7.88 (d, 2H, J=8.4 Hz), 10.00 (s, 1H).

1. customThe reaction mixture was flushed with argon
2. temperaturemaintained under argon
3. temperatureThe mixture was then cooled
4. additiondiluted with EtOAc (35 mL) and water (30 mL)
5. washThe aqueous layer was washed with EtOAc (2×10 mL)
6. dry with materialthe combined organic extracts dried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customPurification of the resultant oil by column chromatography on silica gel (Hexanes/EtOAc, 4:1)