Potassium Carbonate → 4-Bromo-2-(2-oxocyclopentyloxy)anisole

HRID 843647Notes

Reaction equation

HRID 843647 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([Br:10])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Cl[CH:12]1[CH2:16][CH2:15][CH2:14][C:13]1=[O:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([Br:10])=[CH:3][C:2]=1[O:1][CH:12]1[CH2:16][CH2:15][CH2:14][C:13]1=[O:17]

Participants

5

Reactant 3

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

Product 1

HCID 108914134-Bromo-2-(2-oxocyclopentyloxy)anisoleYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 20 g (0.1 mol) of 3-Hydroxy-4-methoxybromobenzene in 300 ml of absolute dimethylformamide is added 17.7 g (0.15 mol) of 2-Chlorocyclopentanone and 41.4 g (0.3 mol) of potassium carbonate. The solution is stirred at room temperature for 12 h. Afterwards the solid substances are filtered off and the filtrate is concentrated. The residue is dissolved in 500 ml of ethyl acetate and washed three times with 200 ml of destined water. The organic layer is dried over sodium sulfate and concentrated. The residue is chromatographed on a silica gel column to give 21.1 g of the title compound as a brown oil. TLC (petroletherdethyl acetate, 6:4), Rf=0.47.

Workup

  1. filtrationAfterwards the solid substances are filtered off
  2. concentrationthe filtrate is concentrated
  3. dissolutionThe residue is dissolved in 500 ml of ethyl acetate
  4. washwashed three times with 200 ml of destined water
  5. dry with materialThe organic layer is dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is chromatographed on a silica gel column

Sources & evidence

ORD record
ord-9b7dc13d2e0a46c3a0e8b0bdf02ae92a
Source dataset
uspto-grants-2002_04
Patent number
US06380196B1

Reaction notes

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