Dimethylformamide → 4-Bromo-2-(3-oxopentan-2-yloxy)anisole

HRID 2084809Notes

Reaction equation

HRID 2084809 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([OH:8])[CH:7]=1.Br[CH:12]([C:14](=[O:17])[CH2:15][CH3:16])[CH3:13].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([O:8][CH:12]([C:14](=[O:17])[CH2:15][CH3:16])[CH3:13])[CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 1422285-Bromo-2-methoxyphenolHCID 5450922-Bromo-3-pentanone

Product 1

HCID 227341244-Bromo-2-(3-oxopentan-2-yloxy)anisole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 5-bromo-2-methoxyphenol (50.0 g), 2-bromo-3-pentanone (68.1 g), potassium carbonate (52.8 g), and DMF (500 ml) was stirred at 70° C. for 2 hours. After being allowed to stand for cooling, water was added to the mixture followed by extraction with ether. The organic layer was washed with a saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (hexane:chloroform=1:1) to give Compound IIb-a (86.8 g, 94.0%) as a pale-yellow oily substance.

Workup

  1. temperaturefor cooling
  2. extractionfollowed by extraction with ether
  3. washThe organic layer was washed with a saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by silica gel column chromatography (hexane:chloroform=1:1)
  7. customto give Compound IIb-a (86.8 g, 94.0%) as a pale-yellow oily substance

Sources & evidence

ORD record
ord-515187bf1116404aaa6b420f9d5c6077
Source dataset
uspto-grants-2004_04
Patent number
US06716987B1

Reaction notes

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