1,10-Phenanthroline → 3-(2-Bromo-3-methylphenoxy)tetrahydrofuran

Participants

Reaction Conditions

Reaction Steps

A vial was charged with copper(I) iodide (38.5 mg, 0.202 mmol), 1,10-phenanthroline (72.8 mg, 0.404 mmol), cesium carbonate (1.32 g, 4.04 mmol), 2-bromo-1-iodo-3-methylbenzene (600 mg, 2.021 mmol) and tetrahydrofuran-3-ol (1.80 mL, 22.23 mmol). The vial was sealed and the reaction mixture was heated to 120° C. for 24 h. The reaction mixture was cooled to RT, EtOAc was added and the mixture was filtered through a pad of silica gel. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (25% EtOAc/hexanes). 3-(2-Bromo-3-methylphenoxy)tetrahydrofuran was isolated as a light-yellow oil (178 mg).

Provenance & Evidence