Finkelstein Reaction of (Chloromethyl)dimethyl(phenyl)silane with Sodium Iodide; (Iodomethyl)dimethyl(phenyl)silane
SyntheticPage 758
DOI:
10.1039/SP758
Submitted Jul 11, 2014, published Aug 11, 2014
Christopher Kelly (
christopher.b.kelly@uconn.edu), Michael Mercadante (
michael.mercadante@uconn.edu), Nicholas Leadbeater (
nicholas.leadbeater@uconn.edu), Leon Tilley (
ltilley@stonehill.edu)
A contribution from
Tilley Group
Chemicals Used
(Chloromethyl)dimethyl(phenyl)silane (Gelest)
Sodium Iodide (ACS reagent, ≥99.5%, Sigma Aldrich)
Acetone (CHROMASOLV® Plus, ≥99.9%, Sigma Aldrich)
Procedure
In a 250 mL round bottom flask equipped with a stir bar was added (chloromethyl)dimethyl(phenyl)silane (20.13 g, 0.108 mol, 1 equiv), acetone (100 mL, 1.08 M) and sodium iodide (28.4 g, 0.189 mol, 1.75 equiv) and allowed to reflux for 24 h. After this time, the reaction was cooled to room temperature and the solvent removed via rotary evaporation to give a slurry. The resulting slurry was passed through a pad of Celite® which was washed with 100 mL of hexanes. The solvent removed via rotary evaporation to give the pure iodide as a clear, colorless liquid (30.1 g, 100%).
Author's Comments
The reaction is quite scaleable and general. It is not limited to the system described here.
Data
1H NMR (400 MHz, CDCl3) d ppm 0.49 (s, 6 H) 2.22 (s, 2 H) 7.37 - 7.48 (m, 3 H) 7.54 - 7.63 (m, 2 H) 13C NMR (100 MHz, CDCl3) d ppm -13.25 (CH2) -2.59 (CH3) 128.25 (CH) 129.89 (CH) 133.94 (CH) 137.06 (C) GC-MS (EI) 276 ([M]+, 8%), 260 (20%), 149 (63%), 135 (100%), 119 (14%) 105 (17%), 92 (14%).
Lead Reference
Mercadante, M.; Kelly, C. B.; Hamlin, T.A., Delle Chiaie, K.; Drago, M.; Duffy, K.; Dumas, M.; Fager, D.; Glod, B.; Hansen, K.; Hill, C.; Leising, R.; Lynes, C.; MacInnis, A.; McGohey, M.; Murray, S.; Piquette, M.; Roy, S.; Smith, R.; Sullivan, K.; Truong, B.; Gorbatyuk, V.; Vailonis, K.; Leadbeater N. E.; Tilley L. J. Chem. Sci. 2014 DOI: 10.1039/C4SC01732C
Other References
Tilley, L. J.; Shiner, V. J., Jr. J. Phys. Org. Chem. 1999, 12, 564.
Supplementary Information
H NMR (iodomethylsilane.jpg)
C13 NMR (iodomethylsilaneC13.jpg)
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Get structure file (.cdx, .sk2, .mol)
Keywords: Alkanes, nucleophilic, Organosilicon, SN2, substitution
