Sodium Iodide → HCID 89405808, compound

Participants

Reaction Steps

1-(3-Chloro-2,6-difluorophenyl)-3-iodopropan-1-one: (Ref: Synthesis, 366-399 (1998)) To a stirred solution of NaI (0.153 g, 1.019 mmol) in ACN (0.637 ml) was added TMS-CI (0.130 mL, 1.019 mmol) dropwise. A precipitate was formed, and the mixture turned yellow. Water (0.015 mL, 0.849 mmol) was added (which re-dissolved the precipitate), followed by addition of Intermediate 2B (0.172 g, 0.849 mmol). The mixture was diluted with additional ACN (0.637 mL), and stirred at rt under argon for 15 min. The reaction mixture was diluted with water and extracted with EtOAc (3×). The combined organic layers were washed with 10% Na2S2O3 and brine, dried over anhydrous MgSO4, filtered, and concentrated to yield the desired product as a light yellow oil (0.265 g, 94%), MS (ESI) m/z: 330.7 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 7.50 (ddd, J=8.9, 8.1, 5.7 Hz, 1H), 6.96 (td, J=8.8, 1.8 Hz, 1H), 3.59-3.53 (m, 2H), 3.45-3.40 (m, 2H).

Provenance & Evidence