Dimethylformamide → 1-[5-Bromo-3-(dimethylamino)-2-methoxyphenyl]-1-ethanone

HRID 1295967Notes

Reaction equation

HRID 1295967 reaction equation
NC1[C:3]([O:12][CH3:13])=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6]([Br:8])[CH:7]=1.IC.C(=O)([O-])[O-].[K+].[K+].[CH3:22][N:23]([CH3:26])[CH:24]=O>C(OCC)(=O)C.O>[Br:8][C:6]1[CH:7]=[C:24]([N:23]([CH3:26])[CH3:22])[C:3]([O:12][CH3:13])=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 229296751-(3-Amino-5-bromo-2-methoxy-phenyl)-ethanone

Product 1

HCID 229296931-[5-Bromo-3-(dimethylamino)-2-methoxyphenyl]-1-ethanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-(3-amino-5-bromo-2-methoxyphenyl)-1-ethanone (12.8 g), iodomethane (60 mL), potassium carbonate (14.4 g) and N,N-dimethylformamide (200 mL) was stirred at 60 to 70° C. for 2 hours. Water was added to the mixture, extraction was performed with ethyl acetate, and the organic layer was washed with brine and then dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (9.6 g) as a yellow oil.

Workup

  1. washthe organic layer was washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationAfter distilling off the solvent under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-5f8f4b21fee84eb9a309debfaa76dac7
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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