iodomethylbenzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Benzyl iodide (280 mg, 1.28 mmol) and anhydrous potassium carbonate (440 mg, 3.2 mmol) were added to a solution of methyl 2-(R)-[benzyl-(methylaminosulfonyl)amino]-3-methylbutyrate (200 mg, 0.64 mmol), [prepared as described in Step 1 above] in DMF (3 ml) at RT. After 96 h, 1 M HCl was added and the product was extracted into ethyl acetate. The organic layer was washed with dilute sodium thiosulfate and brine and dried over MgSO4. The organics were removed in vacuo and the residue was chromatographed (PTLC, SiO2, 20% ethyl acetate/hexane) to give methyl 2-(R)-[benzyl-(benzylmethylaminosulfonyl)amino]-3-methylbutyrate as a colorless oil (60%). the product was extracted into ethyl acetate The organic layer was washed with dilute sodium thiosulfate and brine dried over MgSO4 The organics were removed in vacuo the residue was chromatographed (PTLC, SiO2, 20% ethyl acetate/hexane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Utilizing the material from Example 255 Step A, the title compound was prepared in analogous fashion using benzyl iodide as the alkyl halide and following the procedure of Step B-D of Example 255, as a viscous liquid. 1H NMR (CDCl3, 300 MHz) δ 1.60–2.0 (m, 2H), 2.55–2.95 (m, 4H), 2.95–3.15 (m, 2H), 3.20–3.45 (m, 3H), 4,40 (q, J=16.1 Hz, 2H), 6.41 (d, J=7.1 Hz, 1H), 6.51 (d, J=7.1 Hz, 1H), 6.62 (t, J=7.1 Hz, 1H), 7.20–7.40 (m, 5H) ppm. MS (CI): 306 (M+H+).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-phenyl-3,4-dihydroisoquinoline (1.0 g) and benzyliodide (1.26 g) in acetonitrile (7 ml) was refluxed for 1 hour. After allowing to cool to room temperature, the reaction mixture was evaporated in vacuo and the residual precipitate was recrystallized from a mixture of diethyl ether (5 ml) and acetonitrile (3 ml). The crystal was collected by filtration, washed with diethyl ether and dried in vacuo to give 1-phenyl-2-benzyl-3,4-dihydroisoquinolinium iodide (1.52 g). was refluxed for 1 hour the reaction mixture was evaporated in vacuo the residual precipitate was recrystallized from a mixture of diethyl ether (5 ml) and acetonitrile (3 ml) The crystal was collected by filtration washed with diethyl ether dried in vacuo

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. heated at reflux under an argon atmosphere for 5 h Acetone was removed under vacuum the product was extracted with toluene gave resonances at δ=7.68 (doublet), 7.08 (doublet), 4.03 and 3.45 can be prepared in solution

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. heated at reflux under an argon atmosphere for 5 h Acetone was removed under vacuum the product was extracted with toluene gave resonances at δ=7.68 (doublet), 7.08 (doublet), 4.03 and 3.45 can be prepared in solution