2-Fluoro-1-methoxy-3-methyl-4-nitrobenzene → 3-Fluoro-4-methoxy-2-methylaniline

Participants

Reaction Steps

Iron powder (14.25 g) was added portion wise to a solution of 2-fluoro-1-methoxy-3-methyl-4-nitro-benzene (10.5 g, 90% purity) in acetic acid (350 ml) at room temperature. The resulting brown suspension was stirred during 2 hours at room temperature. The reaction mixture was quenched with concentrated aq NaOH solution and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulphate anhydrous, filtered and concentrated under reduced pressure to obtain 3-fluoro-4-methoxy-2-methyl-phenylamine as orange oil (8.50 g, 90% purity) which was used in Step 4 without any further purification. 1H NMR (CDCl3) δ ppm: 6.66 (1H, dd); 6.38 (1H, dd); 3.80 (3H, s); 3.34 (2H, br s); 2.08 (3H, d).

Provenance & Evidence