Acetic Acid → HCID 23090743, compound

Participants

Reaction Conditions

Reaction Steps

2-Amino-4-bromo-phenol (3.9 g, 20.74 mmol) was dissolved into AcOH (120 mL) and heated to 40° C. To this stirring solution at 40° C. was added (HCHO)n (1.9 g, 62.23 mmol), followed by NaBH3CN (3.9 g, 62.23 mmol). The reaction mixture was stirred for 1 hr at 40° C., then another (HCHO)n (1.9 g, 62.23 mmol) and NaBH3CN (3.9 g, 62.23 mmol) were added. The mixture was stirred for 16 hrs at 40° C. The solvent was removed under reduced pressure. The residues were partitioned between EtOAc and water. The organic layer was collected and dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with ethyl acetate-hexanes (30:70) to afford 4-bromo-2-dimethylamino-phenol as a light yellow solid (3.7 g, 83%): 1H NMR (300 MHz, DMSO-d6): δ 9.44 (s, 1 H), 6.92 (m, 2 H), 6.71 (d, J=8.4 Hz, 1 H), 2.69 (s, 6 H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=20% ethyl acetate in hexanes; Rf=0.57.

Provenance & Evidence