Dimethylformamide → 4-Bromo-2-(2-oxocyclopentyloxy)anisole

HRID 1057929Notes

Reaction equation

HRID 1057929 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([OH:8])[CH:7]=1.[CH2:11]1[CH2:16][C:14](=[O:15])[CH:13](Cl)[CH2:12]1.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:13]2[CH2:12][CH2:11][CH2:16][C:14]2=[O:15])[CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 127512-Chlorocyclopentanone2×HCID 1422285-Bromo-2-methoxyphenol

Product 1

HCID 108914134-Bromo-2-(2-oxocyclopentyloxy)anisole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-bromo-2-methoxyphenol (6.31 g), α-chlorocyclopentanone (6.9 ml), potassium carbonate (9.57 g), and DMF (63 ml) was stirred at 90° C. for 2 hours. α-Chlorocyclopentanone (14 ml) was further added to the mixture, followed by stirring at 90° C. for one hour. 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 1N aqueous solution of sodium hydroxide and then with a saturated saline, and dried over sodium sulfate. The solvent, was distilled off, and the residue was purified by column chromatography (silica gel, hexane:ethyl acetate=2:1) to give Compound IIl-a (11.8 g, 99%) as an oily substance.

Workup

  1. stirringby stirring at 90° C. for one hour
  2. temperaturefor cooling
  3. extractionfollowed by extraction with ether
  4. washThe organic, layer was washed with a 1N aqueous solution of sodium hydroxide
  5. dry with materialwith a saturated saline, and dried over sodium sulfate
  6. distillationThe solvent, was distilled off
  7. customthe residue was purified by column chromatography (silica gel, hexane:ethyl acetate=2:1)
  8. customto give Compound IIl-a (11.8 g, 99%) as an oily substance

Sources & evidence

ORD record
ord-88ffec7cb140476ab14a82c1643c4d6d
Source dataset
uspto-grants-2003_02
Patent number
US06514996B2

Reaction notes

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