Hydroxylamine → Tert-butyl {4-[amino(hydroxyimino)methyl]-2-fluorophenoxy}acetate

Participants

Reaction Steps

Tert-butyl (4-cyano-2-fluorophenoxy)acetate (3.50 g; 13.93 mmol; 1 eq.) was suspended in EtOH (70 mL). hydroxylamine (2.05 mL; 69.65 mmol; 5 eq.) was added in one portion. The reaction mixture was stirred at RT for 12 hours. The reaction mixture was concentrated affording the title compound as a white solid (3.57 g, 90%). 1H NMR (DMSO-d6, 300 MHz) δ 9.61 (br s, 1H), 7.51-7.41 (m, 2H), 7.09-7.03 (t, J=8.84 Hz 1H), 5.81 (br s, 2H), 4.78 (s, 2H), 1.42 (s, 9H). LC/MS (Method 13): 285.1 (M+H)+. HPLC (Method A) Rt 2.91 min (Purity: 94.3%).

Provenance & Evidence