2-Iodotoluene → HCID 9817009, compound

Participants

Reaction Steps

In a 50 mL oven-dried flask was added Mg turnings (780 mg, 32 mmol), which were activated by the use of a heat-gun under vacuum, followed by addition of anhydrous THF (7 mL). Under inert atrnosphere was added a suspension of 2-iodotoluene (5.3 g, 24 mmol) in THF (10 mL) and the reaction mixture was allowed to reflux for 4 hours. A suspension of compound 6 (1.50 g, 8 mmol) in THF (5 mL) was added via a syringe followed by addition of CuBr (23 mg, 0.16 mmol, 2 mol %) and the reaction mixture was stirred at rt overnight. The reaction mixture was quenched by addition of H2SO4 (20 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 0.41 g of crude 7. The crude product was subjected to preparative HPLC CC [eluent: Buffer A: 0.1% TFA; Buffer B: 80% CH3CN+0.1% TFA] to produce an analytical pure sample of compound 7. LC-MS [M+H]+275 (cald. 275.2).

Provenance & Evidence