1-Methyl-3-p-tolyltriazene → 2,6-Difluoro-4-nitroanisole

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Reaction Steps

Dissolve 2,6-difluoro-4-nitrophenol (J. Heterocyclic. Chem. 1976, 13, 1253; 10 g, 57.11 mmol) in 300 mL of benzene. Add dropwise a solution of 1-methyl-3-p-tolyltriazene (9.37 g, 62.82 mmol, 1.1 eq.) in benzene (150 mL). After TLC indicates absence of starting material, transfer the reaction mixture to a separator funnel and wash with 1 N HCl, then saturated NaHCO3, and then water. Dry the organic layer over MgSO4, filter, and remove the solvent to give a residue. Crystallize the residue from MeOH/water to give 1,3-difluoro-2-methoxy-5-nitrobenzene as white needles: 1H NMR (300 MHz, CDCl3): 4.25 (t, 3H), 7.80 (d, 2H).

Provenance & Evidence