反应详情

To a solution of ethyl 3,5-dimethoxyphenylacetate (11.0 g, 52,32 mmol) in 200 ml of CH2Cl2 is added 75 ml (25 mmol, 1.4 eq) of 1.0M BBr3 in CH2Cl2. This is then refluxed for 36 hours. The mixture is concentrated in vacuo, then partitioned between EtOAc and HCl. The organics are dried (MgSO4) and concentrated in vacuo. This is then redissolved in EtOH and HCl is bubbled in for 5 minutes and then stirred overnight at room temperature. The mixture is concentrated in vacuo, then partitioned between EtOAc and saturated NaHCO3 solution. The organics are dried (MgSO4) and concentrated in vacuo. This is then chromatographed using silica gel and eluted with Et2O. The filtrate is concentrated in vacuo to obtain ethyl 3,5-dihydroxyphenylacetate which is confirmed by NMR and used directly in the next step.

1. temperatureThis is then refluxed for 36 hours
2. concentrationThe mixture is concentrated in vacuo
3. custompartitioned between EtOAc and HCl
4. dry with materialThe organics are dried (MgSO4)
5. concentrationconcentrated in vacuo
6. dissolutionThis is then redissolved in EtOH
7. customHCl is bubbled in for 5 minutes
8. concentrationThe mixture is concentrated in vacuo
9. custompartitioned between EtOAc and saturated NaHCO3 solution
10. dry with materialThe organics are dried (MgSO4)
11. concentrationconcentrated in vacuo
12. customThis is then chromatographed
13. washeluted with Et2O
14. concentrationThe filtrate is concentrated in vacuo