反应详情

A solution of 3-bromo-4-methyl-benzenethiol (1.27 g; 6.25 mmol) in anhydrous DMF (12.5 ml) was treated with sodium hydride (300 mg; 7.5 mmol). Then reaction mixture was stirred at RT for 15 minutes, then the treated with 1-iodopropane (0.73 ml; 7.5 mmol). The reaction was stirred for 24 hours, before being quenched by dropwise addition of water. EtOAc was added and the layers separated. The organic layer was washed with brine, dried on MgSO4, filtered and concentrated under reduced pressure. The residue was dissolved in MeOH (13 mL), cooled to 0° C. and treated with a 0.5 M solution of sodium (meta)periodate in water (12.5 ml; 6.24 mmol). After stirring for 24 hours at RT, EtOAc and water were added and the phases separated and the organic phase was dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc to give the title compound as a yellow sticky solid.

1. customThen reaction mixture
2. stirringThe reaction was stirred for 24 hours
3. custombefore being quenched by dropwise addition of water
4. additionEtOAc was added
5. customthe layers separated
6. washThe organic layer was washed with brine
7. customdried on MgSO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. dissolutionThe residue was dissolved in MeOH (13 mL)
11. temperaturecooled to 0° C.
12. stirringAfter stirring for 24 hours at RT
13. customthe phases separated
14. dry with materialthe organic phase was dried over MgSO4
15. concentrationconcentrated under reduced pressure
16. customThe resulting residue was purified by flash column chromatography (silica)
17. washeluting with cyclohexane containing
18. temperatureincreasing amounts of EtOAc