2-Iodotoluene → HCID 9859995, compound

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Reaction Steps

In a 10 mL oven-dried flask was added Mg turnings (116 mg, 4.0 mmol) which were activated under vacuum by the use of a heat-gun. Under inert atmosphere was added a mixture of 2-iodotoluene (0.65 g, 3.0 mmol) in Et2O (3 mL) and the reaction mixture was allowed to reflux for 1 hour. A solution of compound 14 (0.33 g, 2.0 mmol) in CH2Cl2 (3 mL) was added via a syringe and the reaction mixture was stirred at rt overnight. The reaction mixture was quenched by addition of H2SO4 (6 mL, 2 M) and stirred at rt for 2 hours followed by addition of NaOH (8 mL, 2 M). Addition of THF (15 mL) was followed by extraction with CH2Cl2 (3×20 mL). The organic phases were dried (MgSO4) and evaporated to dryness to produce 0.26 g of crude 15. The crude product was subjected to preparative HPLC [eluent: Buffer A: 0.1% TFA; Buffer B: 80% CH3CN +0.1%TFA] to produce an analytically pure sample of compound 15. LC-MS [M+H]+ 260 (cald. 260.4).

Provenance & Evidence