Sodium Iodide → HCID 21995713, compound

Temperature

90 °C

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).

1. stirringthe mixture was stirred for 2 days
2. extractionthe mixture was extracted with ethyl acetate
3. washThe organic layer was washed with water
4. dry with materialdried with magnesium sulfate
5. customUnder reduced pressure, the solvent was evaporated
6. customthe residue was purified with silica gel column chromatography (ethyl acetate/hexane=1:19)
7. distillationdistilled under reduced pressure (0.7 mmHg, 131° C.)

ORD record

ord-6c552b68435d4c9ca7e4002397768136

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06235771B1