Sodium Iodide → Ethyl 5-iodo-2-methylbenzoate

Temperature

110 °C

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%).

1. customThe mixture was evacuated
2. temperatureThe mixture was cooled to room temperature
3. filtrationfiltered off through celite
4. customThe filtrated was evaporated under vacuum
5. customto remove solvent
6. additionThe residue was diluted with EtOAc
7. washwashed with aq. 50% NH4Cl solution
8. dry with materialThe organic layer was dried over anhydrous MgSO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe residue was purified by silica column chromatography

ORD record

ord-513cee849fd94b4bb0a6f8f2b6c89539

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08586550B2