Sodium hydride → HCID 23120690, compound

Participants

Reaction Steps

1.96 g of 5-chloro-4-methyl-1H-indol-2,3-dione was added under ice cooling and a nitrogen atmosphere to a 50 mL tetrahydrofuran solution of 440 mg of sodium hydride, and the reaction mixture was stirred for 1 hour. After this, a previously prepared 15 mL tetrahydrofuran solution of bromo(5-chloro-2-methoxyphenyl)magnesium was added dropwise over a period of 10 minutes. The reaction mixture was stirred for 3 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 another 30 minutes at room temperature. After liquid separation, the aqueous layer was extracted with ethyl acetate (30 mL×3), and 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 then filtered off to obtain 2.43 g of the titled compound (yellow solid).

Provenance & Evidence