Methyl iodide → 3-Bromo-N-methylaniline

2 g (11.6 mmol) 3-Bromoaniline is dissolved in 15 mL DMF and treated with 716 mg (1.1 eq.) KOH and 0.722 mL (1 eq.) iodomethane under continuous stirring at room temperature for 20 hours. The reaction mixture is extracted with ethyl acetate and water, the combined organic phases are washed with brine and dried with sodium sulfate and evaporated to dryness. The residue is column chromatographed (ethyl acetate/petroleum ether 2:5) to yield after evaporation the desired product as a yellow oil.

1. extractionThe reaction mixture is extracted with ethyl acetate and water
2. washthe combined organic phases are washed with brine
3. dry with materialdried with sodium sulfate
4. customevaporated to dryness
5. customchromatographed (ethyl acetate/petroleum ether 2:5)
6. customto yield
7. customafter evaporation the desired product as a yellow oil

ORD record

ord-98d16ed1439c49cbbe927b3143508989

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07632851B2