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

HRID 1057924Notes

Reaction equation

HRID 1057924 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([OH:8])[CH:7]=1.Cl[CH:12]1[CH2:16][CH2:15][CH2:14][C:13]1=[O:17].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]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])[CH:7]=1

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 5-bromo-2-methoxyphenol (120.0 g), 2-chloro-1-cyclopentanone (100.0 g), potassium carbonate (163.3 g), and DMF (1.2 l) was stirred at 70° C. for 3 hours. After being allowed to stand for cooling, water was added to the mixture followed by extraction with ethyl acetate. 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:ethyl acetate=9:1) to give Compound IIc-a (141.43 g, 83.9%) as a pale-yellow oily substance.

Workup

  1. temperaturefor cooling
  2. extractionfollowed by extraction with ethyl acetate
  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:ethyl acetate=9:1)
  7. customto give Compound IIc-a (141.43 g, 83.9%) as a pale-yellow oily substance

Sources & evidence

ORD record
ord-8fa87aa6622846dd97562695a657b5c9
Source dataset
uspto-grants-2003_02
Patent number
US06514996B2

Reaction notes

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