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

HRID 1005379Notes

Reaction equation

HRID 1005379 reaction equation
Cl[CH:2]1[CH2:6][CH2:5][CH2:4][C:3]1=[O:7].C(=O)([O-])[O-].[K+].[K+].[OH:14][C:15]1[CH:16]=[C:17]([Br:23])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]>CN(C=O)C>[CH3:22][O:21][C:20]1[CH:19]=[CH:18][C:17]([Br:23])=[CH:16][C:15]=1[O:14][CH:2]1[CH2:6][CH2:5][CH2:4][C:3]1=[O:7]

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

17.7 g (0.15 mol) of 2-chlorocyclopentanone and 41.4 g (0.3 mol) of potassium carbonate are added to a solution of 20 g (0.1 mol) of 3-hydroxy-4-methoxy-bromobenzene in 300 ml of absolute DMF and the mixture is stirred at RT for 12 h. After filtering off the solids, the filtrate is concentrated, the residue is taken up in 500 ml of ethyl acetate and the solution is extracted by shaking with 3×200 ml of distilled water. Column chromatography affords 21.1 g of the title compound as a brown oil. TLC (petroleum ether/ethyl acetate 6:4), Rf =0.47.

Workup

  1. filtrationAfter filtering off the solids
  2. concentrationthe filtrate is concentrated
  3. extractionthe solution is extracted
  4. stirringby shaking with 3×200 ml of distilled water

Sources & evidence

ORD record
ord-cd76961b39d74620a66a62189074661a
Source dataset
uspto-grants-2000_04
Patent number
US06054475

Reaction notes

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