2-Iodotoluene → HCID 9882866, compound

Participants

Reaction Steps

In a 10 mL oven-dried flask charged with Mg turnings (100 mg, 4.0 mmol) which was activated under vacuum by the use of a heat-gun. Under inert atmosphere was added a suspension of 2-iodotoluene (0.66 g, 3.0 mmol) in Et2O (3 mL) and the reaction mixture was allowed to reflux for 1 hours. A suspension of compound 16 (0.43 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), and the organic phases were dried (MgSO4) and evaporated to dryness to produce 0.50 g of crude 17. 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 17. LC-MS [M+H]+ 302 (cald. 302.5).

Provenance & Evidence