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TCI Practical Example: Sandmeyer Reaction Using tBuONO
We are proud to present the preparation of diazonium salt by using tBuONO followed by the Sandmeyer reaction to introduce the iodo group.
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Used Chemicals
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Procedure
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tert-Butyl nitrite (0.30 mL, 2.5 mmol, 2.5 eq.) was added dropwise to a solution of p-anisidine (123 mg, 1.0 mmol), p-toluenesulfonic acid monohydrate (190 mg, 1.0 mmol, 1.0 eq.) and potassium iodide (415 mg, 2.5 mmol, 2.5 eq.) in acetonitrile (5 mL) at 0 °C. The mixture was stirred at same temperature for 30 minutes. Then the reaction mixture was heated to 60 °C and stirred for 4 hours. After quenching with water (15 mL), the mixture was extracted with ethyl acetate (15 mL x 3) and the organic layer was washed with 2 mol/L HCl aq. (15 mL), sat. NaHCO3 aq. (15 mL) and brine (15 mL), dried over sodium sulfate and filtered. The filtrate was removed under reduced pressure and the residue was purified by column chromatography (on silica gel, ethyl acetate:hexane = 1:4) to give 4-iodoanisole as a red solid (202 mg, 86% yield).
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Experimenter's Comments
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The reaction mixture was monitored by UPLC.
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Analytical Data
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4-iodoanisole
1H NMR (400 MHz, CDCl3); δ 7.56 (d, J = 8.0 Hz, 2H), 6.68 (d, J = 8.0 Hz, 2H), 3.78 (s, 3H).
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Lead Reference
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- A New, One-Step, Effective Protocol for the Iodination of Aromatic and Heterocyclic Compounds via Aprotic Diazotization of Amines
