3-Fluoro-4-nitroanisole → 2-Fluoro-4-methoxyaniline

Participants

Reaction Steps

30 g (0.175 mole) of 3-fluoro-4-nitroanisole was dissolved in 100 mL of ethanol and degassed several times from alternating vacuum/N2. 1.5 g of Pd/C was added and the contents were hydrogenated using a Parr shaker (35 psi). After 30 min. the pressure had dropped to 5 psi, so it was increased to 35 psi and allowed to react for another 2 hrs. No further pressure drop was experienced. Contents were degassed, filtered through Celite and rotoary-evaporated to dryness to give 23.4 g (95%) of desired product. No purification was necessary. 1H NMR (CDCl3, 400 MHz) 6.71 (dd, 1H), 6.62 (d, 1H), 6.53 (d, 1H) 3.73 (s, 3H), 3.43 (bs, 2H).

Provenance & Evidence