Potassium Carbonate → HCID 57894155, compound

HRID 1822346Notes

Reaction equation

HRID 1822346 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5](C=O)=[C:4]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])[CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:26])C=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([OH:26])=[C:4]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 57894228HCID 57894228, compound

Product 1

HCID 57894155HCID 57894155, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 4-chloro-2-(2-fluoro-phenoxy)-benzaldehyde (0.8 g, 3.2 mmol) in chloroform (10 mL) is treated with m-CPBA (2.75 g, 16 mmol). The reaction is heated to reflux and stirred for about 2 hr. The reaction is cooled to room temperature and quenched with 10% aqueous NaHSO4. The aqueous is extracted with diethyl ether. The organic is washed with brine, dried over sodium sulfate, and the solvent is removed. The crude is diluted in methanol (20 mL) and treated with potassium carbonate (1.32 g, 9.6 mmol). The reaction stirred for 30 minutes at room temperature. The reaction is filtered and the solvent removed. The crude is purified by silica gel column chromatography using 4:1 hexanes:acetone to elute the pure product. The solvent is removed to afford about 0.64 g (84%) of product. 1H NMR (400 MHz, CDCl3). MS (ES−) m/z mass calcd for C12H8ClFO2 238, found 237 (M−1, 100%).

Workup

  1. temperatureThe reaction is heated
  2. temperatureto reflux
  3. customquenched with 10% aqueous NaHSO4
  4. extractionThe aqueous is extracted with diethyl ether
  5. washThe organic is washed with brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent is removed
  8. additionThe crude is diluted in methanol (20 mL)
  9. stirringThe reaction stirred for 30 minutes at room temperature
  10. filtrationThe reaction is filtered
  11. customthe solvent removed
  12. customThe crude is purified by silica gel column chromatography
  13. washacetone to elute the pure product
  14. customThe solvent is removed

Sources & evidence

ORD record
ord-7a1cead1ab7b44fcabc77ffc91b5b183
Source dataset
uspto-grants-2009_10
Patent number
US07608639B2

Reaction notes

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