Sodium Iodide → HCID 22347799, compound

Participants

Reaction Steps

1-3-Iodopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (14a). A solution/suspension of 1-(3-chloropropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (20 g, 35 mmol, 80% pure) and sodium iodide (285 g, 1.9 mol) in dry acetone (200 ml) was heated at reflux for 24 h. The mixture was evaporated, and partitioned between ether and water. The ether layer was separated, and was washed successively with water and brine. The organic extract was dried over anhydrous magnesium sulfate, filtered and evaporated to give 1-(3-iodopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (25.8 g, 99%, 80% pure) as a thick oil. 1H NMR (CDCl3) δ 1.6-1.9 (m, 2H), 2.21 (ddd, 1H), 2.31 (ddd, 1H), 3.16 (td, 2H), 5.12 (dt, 1H), 5.21 (dt, 1H), 7.02 (t, 2H), 7.41 (d, 2H), 7.43 (d, 1H), 7.51 (s, 1H), 7.62 (dq, 1H)

Provenance & Evidence