2-Fluoro-6-nitroanisole → 3-Fluoro-2-methoxyaniline

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Reaction Steps

A mixture containing 1-fluoro-2-methoxy-3-nitrobenzene (36.30 g, 0.21 mol), palladium on carbon (10% w/w, ˜8 g), and methanol (200 mL) is stirred under an atmosphere of hydrogen (1 atm) for 27 h. The mixture is filtered and the resulting solution is evaporated to dryness under reduced pressure to give 11 as a brown oil. This product is of sufficient purity (≧95% by NMR spectroscopy) to use directly in the next synthetic step. 1H NMR (CDCl3): δ 3.75 (br, 2H, NH2), 3.91 (d, JH-F=1.5 Hz, 3H, OCH3), 6.46 (m, 2H, overlapping H-4 and H-6), 6.79 (apparent t of d, JH-H=8.0 Hz, JH-F=5.5 Hz, 1H, H-5). 19F{1H} NMR (CDCl3): δ −132.5 (s). 13C{1H} NMR (CDCl3): δ 60.7 (d, JC-F=5.0 Hz, OCH3), 106.1 (d, JC-F=19.5 Hz, C-4), 110.9 (d, JC-F=2.5 Hz, C-6), 123.7 (d, JC-F=9.5 Hz, C-5), 134.9 (d, JC-F=13.0 Hz, C-2), 141.3 (d, JC-F=5.0 Hz, C-1), 154.4 (d, JC-F=244.0 Hz, C-3). LCMS m/z calcd for C7H8FNO ([M]+) 141. Found 142 ([M+H]+).

Provenance & Evidence