Citric Acid → 2-Fluoro-1,3-dimethoxy-4-nitrobenzene

Participants

Reaction Steps

A freshly prepared solution of sodium methoxide [0.58 g (25 mmol) of sodium dissolved in 3 mL of anhydrous methanol] was added dropwise to a solution of 2 g (11.2 mmol) of 1,2,3-trifluoro-4-nitrobenzene in 30 mL of anhydrous methanol under nitrogen at +4° C. The resulting mixture was stirred overnight at room temperature and quenched with 1 M aqueous citric acid (0.1 eq) and methanol was evaporated under reduced pressure. The residue was taken up with ether, washed with 1 M citric acid, brine and dried over anhydrous magnesium sulfate and filtered off. The filtrate was evaporated under reduced pressure to give 2.2 g (99% yield) of the crude product, which was purified by crystallisation from hexane. H1 NMR (CDCl3) 3.95 (s, 3H, OMe); 4.06 (d, 3H, J=1.6 Hz); 6.72 (dd, 1H, CH, J=9.4 Hz, J=7.5 Hz) 7.72 (dd, 1H, CH, J=9.4 Hz, J=2.23 Hz).

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