Sodium Iodide → HCID 21995713, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-N-methylaniline (18.18 g) in DMF (150 ml) were added at room temperature potassium carbonate (25.8 g), sodium iodide (28.0 g) and 2-bromoethylethyl ether (21 ml), and the mixture was stirred at 90° C. for 4 days. To the mixture were added 2-bromoethylethyl ether (10.0 ml), potassium carbonate (20.0 g) and sodium iodide (13.3 g), and the mixture was stirred for 2 days. To the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brined and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography (ethyl acetate/hexane=1:19) and distilled under reduced pressure (0.7 mmHg, 131° C.) to give yellow oil of 4-bromo-N-(2-ethoxyethyl)-N-methylaniline (17.63 g).

Provenance & Evidence