Dimethylformamide → HCID 57671711, compound

HRID 871980Notes

Reaction equation

HRID 871980 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[O:9][CH3:10].[C:11](=[O:14])([O-])[O-].[K+].[K+].[CH3:17]N(C)C=O>C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:17][O:14][CH3:11])=[CH:4][C:3]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 3479554-Bromo-3-methoxyphenol

Product 1

HCID 57671711HCID 57671711, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-bromo-3-methoxyphenol (500 mg, 2.46 mmol), chlorodimethylether (281 μL, 3.70 mmol), and potassium carbonate (850 mg, 6.15 mmol) was suspended in anhydrous N,N-dimethylformamide (8 mL) and stirred at 50° C. for 1 hour. After cooling down, the reaction mixture was diluted with ethyl acetate (150 mL). The mixture was washed with water (150 mL) and saturated brine (50 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (421 mg) as a colorless oil. (Yield 69%)

Workup

  1. temperatureAfter cooling down
  2. washThe mixture was washed with water (150 mL) and saturated brine (50 mL) successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-2b05fb17aca34a2e8674caa9f12b428d
Source dataset
uspto-grants-2015_03
Patent number
US08975256B2

Reaction notes

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