Tetrahydrofuran → 5-Chloro-3-hydroxy-3-(3-methoxyphenyl)-1,3-dihydro-2H-indol-2-one

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Reaction Steps

A solution of 3-methoxyphenylmagnesium bromide is prepared from 3.5 g of magnesium in 10 ml of THF and from a solution of 25 g of 1-bromo-3-methoxybenzene in 40 ml of THF. This solution is added dropwise, under a nitrogen atmosphere, to a mixture of 8 g of 5-chloro-1H-indole-2,3-dione in 50 ml of THF, while keeping the temperature of the reaction medium below 40° C., followed by refluxing for 1 hour. The reaction mixture is cooled to RT, poured into saturated NH4Cl solution and extracted with EtOAc, the organic phase is washed with water and dried over Na2SO4, and the solvent is evaporated off under vacuum. 9.1 g of the expected product are obtained after crystallization from hot iso ether; m.p.=212° C.

Provenance & Evidence