4-Fluoroiodobenzene → HCID 59375138, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-bromo-3,4-dihydroisoquinolin-1(2H)-one (Intermediate 23-1, 60 mg, 0.265 mmol), 1-fluoro-4-iodobenzene (118 mg, 0.531 mmol), potassium carbonate (36.7 mg, 0.265 mmol) and copper (I) iodide (10.11 mg, 0.053 mmol) in DMF (1.000 mL) was heated at 130° C. for 5 h. The mixture was cooled to rt and filtered through a Celite pad, and the solids were washed with EtOAc. The filtrate was washed with water and brine, dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 90:10 to 60:40 hexane-EtOAc) to give 7-bromo-2-(4-fluorophenyl)-3,4-dihydroisoquinolin-1(2H)-one (40 mg, 47%). 1H NMR (400 MHz, chloroform-d) δ 7.15-7.27 (4 H, m), 7.04-7.13 (2 H, m), 6.48 (1 H, d, J=1.94 Hz), 2.96-3.08 (2 H, m), 2.73-2.84 (2 H, m). Mass spectrum m/z 320, 322 (M+H)+.

Provenance & Evidence