Sodium hydride → 4,5-dichloro-3-hydroxy-3-(2-methoxy-5-methylphenyl)-1,3-dihydro-2H-indol-2-one

Participants

Reaction Steps

1.50 g of 4,5-dichloro-1H-indol-2,3-dione was added under ice cooling and a nitrogen atmosphere to a 40 mL tetrahydrofuran solution of 310 mg of sodium hydride, and the reaction mixture was stirred for 1 hour. After this, 20 mL of a previously prepared tetrahydrofuran solution of bromo(2-methoxy-5-methylphenyl)magnesium was added dropwise over a period of 20 minutes, and the reaction mixture was stirred for 4.5 hours at the same temperature, after which 50 mL of a saturated ammonium chloride aqueous solution was added, and the reaction mixture was stirred for 30 minutes at room temperature. After liquid separation, the aqueous layer was extracted with ethyl acetate (30 mL×3), the combined organic layer was washed with saturated brine and dried with sodium sulfate, and the drying agent was then filtered off and the solvent was distilled off under reduced pressure. The residue thus obtained was stirred and washed with isopropyl ether and the solids were filtered off to obtain 1.23 g of the titled compound (yellow solid).

Provenance & Evidence