反应详情

To a DMF (0.2 M) suspension of cesium carbonate (3 eq.) and 5-bromo-2-mercaptobenzoic acid (1 eq.) was added iodomethane (5 eq.). The resulting suspension was then stirred at RT for 1 h. The volatiles were removed before EtOAc and sat. aq. NH4Cl were added. The organic phase was separated, dried over Na2SO4, filtered and the filtrate concentrated in vacuo to a pale yellow oil. This was taken up again in DMF (0.2 M) and added sequentially sodium hydride (3 eq.) and iodomethane (5 eq.). The reaction vessel was then sealed and heated to 70° C. for 16 h. After cooling to RT, EtOAc and sat. aq. NH4Cl were added to the crude reaction mixture. The organic phase was separated, dried over MgSO4, filtered and the filtrate concentrated in vacuo to a brown oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→3:2 (v/v) Hex:EtOAc) afforded the title compound as a light yellow solid.

1. customThe volatiles were removed before EtOAc and sat. aq. NH4Cl
2. additionwere added
3. customThe organic phase was separated
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationthe filtrate concentrated in vacuo to a pale yellow oil
7. customThe reaction vessel was then sealed
8. temperatureheated to 70° C. for 16 h
9. temperatureAfter cooling to RT
10. customreaction mixture
11. customThe organic phase was separated
12. dry with materialdried over MgSO4
13. filtrationfiltered
14. concentrationthe filtrate concentrated in vacuo to a brown oil
15. customPurification of the crude product
16. customthus obtained by way of flash chromatography (SiO2, Hex→3:2 (v/v) Hex:EtOAc)