Sodium Iodide → Ethyl 5-iodo-2-methylbenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of bromide 3 (39.0 g, 161 mmol) in 1,4-dioxane (150 mL) were added NaI (48.2 g, 321 mmol), CuI (1.6 g, 8.03 mmol) and N,N′-dimethylethyldiamine (1.8 mL, 16.1 mmol). The mixture was evacuated and backfilled with N2. The mixture was stirred at 110° C. for 15 h. The mixture was cooled to room temperature and filtered off through celite. The filtrated was evaporated under vacuum to remove solvent. The residue was diluted with EtOAc and washed with aq. 50% NH4Cl solution. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica column chromatography to provide the titled compound 4 (41.3 g, 89%).

Provenance & Evidence