2,5-Dichloronitrobenzene → HCID 15229161, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (0.66 q) Was added in portions to a stirred solution of 3.90 g of 2-hydroxy-4-methoxybenzaldehyde in N,N'-dimethylformamide (70 mL) under nitrogen. To the resulting milky, green mixture was added 1,4-dichloro-2-nitrobenzene (4.47 g). The reaction was placed in an oil bath and stirred at 90° C. for 16 hours. The reaction was then evaporated and the residue partitioned between chloroform (75 mL) and 1 N NaOH (50 mL). The layers were separated and the aqueous layer was extracted with chloroform (75 mL). The chloroform extracts were combined and washed with water (75 mL) and brine (75 mL), dried over magnesium sulfate, and evaporated in vacuo. The orange solid was recrystallized from ethyl acetate/iso-propyl ether to yield 3.86 g (53.9%) of product as light yellow, shiny crystals. Melting Point: 130°-131° C.

Provenance & Evidence