Benzene → 2-Chloro-4-fluoro-1-nitrobenzene

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Reaction Steps

m-Chlorofluorobenzene (240 g. 1.85 moles) is added to a mixture of sulfuric acid (185 g. 1.85 moles) and nitric acid (166 g., 1.85 moles) at -5° C. in 3.5 hours, stirred 13 hours, then benzene (200 ml.) and hexane (200 ml.) are added. The extract is washed with water (1 × 300 ml.), are added. The extract is washed with water (1 × 300 ml.), sodium carbonate solution (1 × 300 ml.), and water (1 × 300 ml.), dried and the solvents removed. The residue is distilled to give 138 g. of mixed isomers. The 4-nitro isomer crystallizes and is filtered off to give 3-chloro-4-nitro-fluorobenzene (51 g. 16.7%) m.p. 36°-38° C.

Provenance & Evidence