2,5-Dichloronitrobenzene → HCID 19102558, compound

Participants

Reaction Conditions

Reaction Steps

0.85 g of sodium hydride was added in portions to a stirred solution of 5.00 g of 2-hydroxy-5-methoxybenzaldehyde in 90 mL of N,N'-dimethylformamide under nitrogen. To the resulting milky, green mixture was added 5.74 g of 1,4-dichloro-2-nitrobenzene. The reaction was placed in an oil bath and stirred at 90° C. for 16 hours. The reaction was then evaporated in vacuo, and the residue partitioned between 75 mL of chloroform and 75 mL of 1 N NaOH. The layers were separated and the aqueous layer was extracted With 75 mL of chloroform. The chloroform extracts were combined and washed with water (2×75 mL) and brine (75 mL), dried over magnesium sulfate, and evaporated in vacuo. The semi-solid residue was triturated with diethyl ether. The precipitated product was collected by filtration, washed with ether, and dried in vacuo to yield 5.96 g (64.8%) of product as a yellow solid. Melting Point: 127°-128° C.

Provenance & Evidence