反应详情

温度

100 °C

A mixture of 4.9 g (0.028 mole) of 2-chloro-4-fluoro-5-aminobenzyl alcohol, 4.25 g (0.028 mole) of tetrahydrophthalic anhydride, and 100 ml of tetrahydrofuran was refluxed overnight. The solvent was evaporated under reduced pressure, leaving a thick, black oil. To this residue was added 100 ml of acetic acid, and the mixture was heated at 100° C. for several hours. The solvent was evaporated under reduced pressure and was replaced with 200 ml of ethyl acetate. This solution was washed three times with 150 ml of a saturated, aqueous solution of sodium bicarbonate and three times with 150 ml of 10% hydrochloric acid. The solution was dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure, leaving 8.80 g of a viscous, black oil. This oil was passed through a column of silica gel, eluting with ethyl acetate/heptane (7/13). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure, yielding 6.3 g of N-[4-chloro-2-fluoro- 5-(methylcarbonyloxymethyl)phenyl]-3,4,5,6-tetrahydrophthalimide as a thick, amber oil. The nmr and ir spectra were consistent with the proposed structure.

1. temperaturewas refluxed overnight
2. customThe solvent was evaporated under reduced pressure
3. customleaving a thick, black oil
4. customThe solvent was evaporated under reduced pressure
5. washThis solution was washed three times with 150 ml of a saturated, aqueous solution of sodium bicarbonate and three times with 150 ml of 10% hydrochloric acid
6. dry with materialThe solution was dried over anhydrous magnesium sulfate
7. filtrationfiltered
8. customthe solvent was evaporated under reduced pressure
9. customleaving 8.80 g of a viscous, black oil
10. washeluting with ethyl acetate/heptane (7/13)
11. customthe solvent was evaporated under reduced pressure