1,10-Phenanthroline → 1-Bromo-4-(cyclohexyloxy)benzene

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of 1-bromo-4-iodo-benzene, (1.00 g, 3.53 mmol), o-phenanthroline (255 mg, 1.41 mmol) and cyclohexanol (1.770 g, 17.67 mmol) in toluene (1.500 mL) was added copper(I) iodide (135 mg, 0.707 mmol) and Cs2CO3 (2.879 g, 8.837 mmol). The resulting mixture was then stirred at 120° C. in a sealed tube for 15 hours. The solvent was then removed under reduced pressure and the product was purified by flash chromatography (eluted by hexane). 1H NMR (400 MHz, MeOD) δ1.32-1.65 (m, 6H), 1.77-1.86 (m, 2H), 1.94-2.03 (m, 2H), 4.24-4.37 (m, 1H), 6.81-6.90 (m, 2H), 7.36-7.41 (m, 2H).

Provenance & Evidence