Hexahydrophthalic anhydride → 1H-Isoindole-1,3(2H)-dione, 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5,6,7-tetrahydro-

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Reaction Steps

2-Chloro-4-fluoro-5-aminophenol (6.6 g) and 2,4,5,6-tetrahydrophthalic anhydride (6 g) are dissolved in acetic acid (20 ml) and refluxed for 2 hours. The resultant mixture is allowed to cool to room temperature and poured into ice-water, followed by extraction with ether. The ether extract is washed with a saturated sodium hydrogen carbonate solution and water in order, dried over anhydrous magnesium sulfate and concentrated. The residue is purified by silica gel-chromatography to give 4.0 g of N-(4-chloro-2-fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide. M.P., 151° C.

Provenance & Evidence