Nitric Acid → 1-Chloro-2,5-dimethyl-3-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

To a solution of commercially available 2-chloro-1,4-dimethylbenzene (5 mL, 37 mmol) in concentrated H2SO4 (5 mL) cooled to 0-5° C. was added dropwise concentrated HNO3 (4.7 mL, 74.6 mmol) over 20 min. After the addition, the reaction was stirred at 0-5° C. for 30 min, then poured carefully into a mixture of ice and saturated aqueous K2CO3 solution (40 mL), and extracted with EtOAc (3×). The combined EtOAc extracts were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was chromatographed (silica gel), eluting with 10-30% EtOAc/hexane to give a mixture of the title compound and its regioisomer (1-chloro-2,5-dimethyl-4-nitrobenzene) (3.0 g). The mixture was further chromatographed (silica gel) eluting with 10% CH2Cl2 in hexane to afford pure compound 19A (0.2 g).

Provenance & Evidence