5-Iodo-1-Indanone synthesis

Yield: 90%

Reaction Conditions:

with copper(l) iodide;tert.-butylnitrite;diiodomethane;iodine in tetrahydrofuran

Steps:

6-Iodo-1-indanone (4a). Procedure B
General procedure: Iodine (5.17 g, 20.4 mmol), CuI (4.66 g, 24.5 mmol), CH₂I₂ (4.93 mL, 61.2 mmol), and tert-butyl nitrite (7.3 mL, 61.2 mmol) were added to a solution of 3a (3.0 g, 20.4 mmol) in dry THF (40 mL). The reaction mixture was stirred at 66 °C for 30 min, cooled to rt, and filtered. The filtrate was concentrated under reduced pressure and extracted with EtOAc. The organic phase was separated, dried over anhydrous Na₂SO₄, filtered, and evaporated. The residue was purified by column chromatography (10 → 20% EtOAc/hexane) to give 4a (4.9 g, 93%) as a white solid.

References:

Howlader, A. Hasan;Diaz, Keili;Mebel, Alexander M.;Kaiser, Ralf I.;Wnuk, Stanislaw F. [Tetrahedron Letters,2020,vol. 61,# 43,art. no. 152427] Location in patent:supporting information