Hydrochloric Acid → HCID 42596963, compound

Participants

Reaction Conditions

Reaction Steps

To a 250 mL flask which contained the suspension of 3-[2-fluoro-3-(4-fluoro-benzyl)-6-methoxy-phenoxy]-phenylamine (P-02) (135 mg, 0.4 mmole) in aq HCl (12 N. 5 mL) was slowly added the solution of sodium nitrite (50 mg, 0.7 mmole) in water (3 mL) at 0° C. The mixture was allowed to stir at 0° C.-5° C. for 1 h, and then was cooled to 0° C. A solution of copper(I) chloride (55 mg, 0.4 mmol) in aq. HCl (12 N. 2 mL)) was added at 0° C. and the reaction mixture which resolved was allowed warm to rt and stir at rt for 1 h. The mixture was poured into 50 mL ice-water, extracted with ethyl acetate (3×30 mL), washed with water (2×30 mL), NaHCO3 (sat. 30 mL), brine (30 mL) and dried over Na2SO4. After removal of solvent, the residue was purified by Prep TLC with ethyl acetate/Hexane as eluent to give 45 mg (33% yield) of product P-03.

Provenance & Evidence