反应详情

温度

23 °C

To a solution of commercially available rhodium(II) octanoate dimer (Rh2(C7H16CO2)4) ([CAS No. 73482-96-9], 160 mg, 1 mol %) in DCM (60 ml) at 45° C. was added a solution of (5-bromo-2-fluoro-phenyl)-diazo-acetic acid allyl ester (intermediate B4A) (6.0 g, 20 mmol) in DCM (2×20 ml) via syringe pump within 16 h. Continued refluxing for 1 h, cooled to 23° C., washed with 1 M aqueous hydrochloric acid (HCl) and sat. aqueous sodium hydrogencarbonate solution (NaHCO3-sol.), dried organic layer over sodium sulfate. Removal of the solvent in vacuum left a green solid, which was purified by silica gel column chromatography with n-heptane/ethyl acetate to give the title compound as a light green solid (4.6 g, 85%) [cf. Adv. Synth. Catal. 2001, 343, 299, for an enantioselective version of this reaction].

1. temperatureContinued refluxing for 1 h
2. washwashed with 1 M aqueous hydrochloric acid (HCl) and sat. aqueous sodium hydrogencarbonate solution (NaHCO3-sol.), dried organic layer over sodium sulfate
3. customRemoval of the solvent in vacuum
4. waitleft a green solid, which
5. customwas purified by silica gel column chromatography with n-heptane/ethyl acetate