2-(2-iodoethoxy)propane synthesis

Yield:318958-37-1 77%

Reaction Conditions:

with sodium iodide in acetone at 60; for 16 h;

Steps:

101

In a round bottom flask were combined toluene-4-sulfonic acid 2-isopropoxy-ethyl ester (1.41 g, 5.45 mmol) and sodium iodide (1.06 g, 7.09 mmol) in acetone (15 mL). The reaction mixture was then heated at 60° C. for 16 h. After this time the reaction was then cooled to 25° C. and the solids were filtered off and washed with acetone. The filterate was then concentrated in vacuo. This residue was then treated with methylene chloride and the solids filtered off. The filterate was then concentrated in vacuo to afford 2-(2-iodo-ethoxy)-propane (896 mg, 77%) as a light yellow oil: EI-HRMS m/e calcd for C₅H₁₁IO (M⁺) 213.9855, observed 213.9860; ¹H NMR(300 MHz, CDCl₃) δ 1.81 (d, J=6.2 Hz, 6 H, 2×CH₃), 3.23 (t, J=7.0 Hz, 2 H, ICH₂), 3.66 (m, 1 H, OCH), 3.69 (t, J=7.0 Hz, 2 H, OCH₂).

References:

US2008/21032,2008,A1 Location in patent:Page/Page column 89