Ammonium Chloride → HCID 67070111, compound

Participants

Reaction Steps

step 3 To a solution of 116 (0.19 g, 0.49 mmol) in MeOH-water (1:1, 20 mL) was added NH4Cl (0.26 g, 4.9 mmol) and iron powder (0.14 g, 2.5 mmol). The resulting mixture was heated at reflux and stirred for 1 h. After cooling to RT, the mixture was filtered through a pad of diatomaceous earth which was washed with MeOH. The filtrate was concentrated under reduced pressure and the resulting aqueous fraction was extracted with EtOAc. The extracts were washed with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with EtOAc/hexane to afford 0.24 g (64%) of 4-(5-bromo-3-tert-butyl-2-methoxybenzyloxy)phenylamine (118) as a yellow oil.

Provenance & Evidence