Diethyl Ether → 5-Chloro-3-hydroxy-3-(2-methoxyphenyl)indolin-2-one

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Reaction Steps

This compound is prepared according to the procedure described in WO 95/18105. A solution of 2-methoxyphenylmagnesium bromide is prepared from 16 g of magnesium in 35 ml of ether and a solution of 124 g of 1-bromo-2-methoxybenzene in 175 ml of ether. This solution is added dropwise, under an argon atmosphere, to a mixture of 30 g of 5-chloro-1H-indole-2,3-dione in 250 ml of THF, cooled beforehand in an icebath, and the mixture is then left stirring and the temperature is allowed to return to RT. After stirring for 1 hour at RT, the reaction mixture is poured slowly into saturated NH4Cl solution and the THF is evaporated off under vacuum. The precipitate formed is filtered off by suction and washed with iso ether. 42 g of the expected product are obtained, and are used without further purification in the following step.

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