反应详情

A mixture of 1-bromo-4-(trifluoromethoxy)benzene (2.41 g), tris(dimethylamino)borane (1.43 g), sodium t-butoxide (1.34 g), tris(dibenzylideneacetone)dipallidium (18 mg), and o-tolylphosphine (12 mg) in toluene (30 ml) was heated under reflux for 4 h. The mixture was cooled, diluted with water (30 mL) and extracted with ethyl acetate (3×10 mL). The combined organic fractions were washed with brine, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with hexane/EtOAc (99:1 increasing to (95:5) to give the title compound as an oil (600 mg). 1H NMR (360 MHz, CDCl3) δ2.95 (6 H, s), 6.66 (2 H, d, J 9 Hz), and 7.08 (2 H, d, J 8.5 Hz). m/z (ES+) m/z 206 (M+1).

1. temperaturewas heated
2. temperatureunder reflux for 4 h
3. temperatureThe mixture was cooled
4. extractionextracted with ethyl acetate (3×10 mL)
5. washThe combined organic fractions were washed with brine
6. dry with materialdried (MgSO4)
7. customthe solvent was evaporated under reduced pressure
8. customThe residue was purified by chromatography on silica gel
9. washeluting with hexane/EtOAc (99:1 increasing to (95:5)