1,2-Dimethyl-3-nitrobenzene → HCID 18629320, compound

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Reaction Steps

The mixture of 90.60 g of 2,3-dimethylnitrobenzene (3-10) and 1.20 g of iron powder was heated at 75° C., to which 115.00 g of bromine was dropped with stirring, and then the resulting mixture was stirred at the same temperature for 4 hours. The reaction solution was poured into ice water, and extracted with ethyl acetate, and the resulting organic layer was washed with sodium thiosulfate solution and saturated salt water in order, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and 400 ml of methanol and 400 ml of concentrated hydrochloric acid were added to the resulting residue, to which 100 g of iron powder was added in a divided form, and thereafter, the resulting mixture was stirred at 70° C. for 30 minutes. The reaction solution was poured into ice water, and the resulting mixture was alkaline with sodium bicarbonate, and thereafter, extracted with ethyl acetate and the resulting organic layer was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent; hexane:ethylacetate=9:1) to obtain 48.82 g of 5-bromo-2,3-dimethylaniline (3-11).

Provenance & Evidence