反应详情

To a mixture of 2-Formyl-5-(4-trifluoromethyl-phenyl)-thiophene-3-boronic acid (0.330 g, 1.10 mmole), 2-Bromo-propene (0.399 g, 3.30 mmole) and cesium fluoride (0.585 g, 3.85 mmole) in dioxane (5 mL), is bubbled with nitrogen gas for 15 minutes. The catalyst PdCl2 (dppf) (0.033 g) is then added to the mixture. The reaction is heated under reflux for 16 hours. The solvent is removed on rota vapor, and the resulting residue is partitioned between ethyl acetate (20 ml) and water (20 mL). The aqueous layer is extracted with more ethyl acetate (20 mL). The combined organic solution is washed with brine (3×50 mL), dried over Na2SO4 and concentrated. The crude product is purified on a silica gel column, eluting with 0-15% ethyl acetate in hexane and concentrated to provide the titled compound as pale yellow crystalline.

1. customis bubbled with nitrogen gas for 15 minutes
2. additionThe catalyst PdCl2 (dppf) (0.033 g) is then added to the mixture
3. temperatureThe reaction is heated
4. temperatureunder reflux for 16 hours
5. customThe solvent is removed on rota vapor
6. customthe resulting residue is partitioned between ethyl acetate (20 ml) and water (20 mL)
7. extractionThe aqueous layer is extracted with more ethyl acetate (20 mL)
8. washThe combined organic solution is washed with brine (3×50 mL)
9. dry with materialdried over Na2SO4
10. concentrationconcentrated
11. customThe crude product is purified on a silica gel column
12. washeluting with 0-15% ethyl acetate in hexane
13. concentrationconcentrated