反应详情

A 5-liter 3-neck round bottom flask was equipped with a mechanical stirrer and nitrogen inlet. Methylene chloride (2 liters) was placed in the reaction flask and terephthalic acid mono-t-butyl ester (127.5 g), 4-dimethylaminopyridine (70.06 g), and 4-chlorobenzenesulfonamide (110.04 g) were added sequentially using methylene chloride (400 ml) to wash down the solids. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride was added in portions over 10 min using methylene chloride (100 ml) to wash down the solid. After the reaction mixture was stirred overnight at room temperature, it was evaporated to dryness. The residue was partitioned between ethyl acetate and water. The organic solution was washed with 20% (w/v) aqueous citric acid, saturated aqueous NaHCO3 and brine; dried (Na2SO4); and evaporated to a white solid. After drying in a vacuum oven at 50°, the ester (277 g, 100%) was obtained in a sufficiently pure state to be used directly for the next step; TLC, Rf =0.43, methanol:chloroform (15:85). (Further purification was possible by recrystallization from ethanol/water; mp above 300°).

1. customA 5-liter 3-neck round bottom flask was equipped with a mechanical stirrer and nitrogen inlet
2. washto wash down the solids
3. addition1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride was added in portions over 10 min
4. washto wash down the solid
5. customit was evaporated to dryness
6. customThe residue was partitioned between ethyl acetate and water
7. washThe organic solution was washed with 20% (w/v) aqueous citric acid, saturated aqueous NaHCO3 and brine
8. dry with materialdried (Na2SO4)
9. customand evaporated to a white solid
10. customAfter drying in a vacuum oven at 50°