Sodium Iodide → [4-(Iodomethyl)phenyl](trimethoxy)silane

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A solution of 1.7 grams of 4-chloromethylphenyltrimethoxysilane, UTF-24M, in 60 mL of dry acetone was stirred with 1.7 g of NaI and heated at reflux under an argon atmosphere for 5 h. The reaction was performed under yellow Safelight conditions. Acetone was removed under vacuum, and the product was extracted with toluene. The resulting colorless to light yellow liquid was stored as a 0.067M stock solution in toluene. The iodinated silane will be referred to as UTF-24I. A 1H NMR spectrum of UTF-24I in C6D6 exhibited resonances at δ=7.61 (doublet) and 7.02 (doublet) for the aromatic ring protons, δ=3.86 for the benzylic protons, and δ=3.43 for the methoxy protons. These values are in comparison to the 1HNMR spectrum for the chloro (UTF-24M) starting material, which gave resonances at δ=7.68 (doublet), 7.08 (doublet), 4.03 and 3.45. The upfield shift of the benzylic protons is consistent with replacement of chlorine by the less electronegative iodine atom. See the monograph by: E. D. Becker, "High Resolution NMR", Academic Press, New York, pg. 73 (1969). This example demonstrates that a benzyl iodide containing silane can be prepared in solution.

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