2-Iodotoluene → HCID 10177007, compound

Participants

Reaction Steps

In a 10 mL oven-dried flask was charged Mg turnings (30 mg, 1.2 mmol) which were activated under vacuum by the use of a heat-gun. Under inert atmosphere was added a solution of 2-iodotoluene (0.22 g, 1.0 mmol) in Et2O (2 mL) and the reaction mixture was allowed to reflux for 1 hour. A mixture of 4-pyrrolidin-1-yl-butyronitrile (Burckhalter et. al. J. Org. Chem. 1961, 26, 4070-4076) (0.14 g, 1.0 mmol) in CH2Cl2 (2 mL) was added via a syringe and the reaction mixture was stirred at rt overnight. The reaction mixture was quenched by addition of H2SO4 (10 mL, 2 M) and stirred at rt for 2 hours followed by addition of NaOH (10 mL, 2 M). Addition of THF (15 mL) was followed by extraction with ethyl acetate (3×20 mL), and the organic phases were dried (MgSO4) and evaporated to dryness to produce 0.12 g of crude 13. The crude product was subjected to preparative HPLC [eluent: Buffer A: 0.1% TFA; Buffer B: 80% CH3CN+0.1% TFA] to produce an analytical pure sample of compound 13. LC-MS [M+H]+ 231 (cald. 231.3).

Provenance & Evidence