4-Fluorophenol → HCID 68859859, compound

HRID 1726026Notes

Reaction equation

HRID 1726026 reaction equation
Br[CH:2]1[CH2:7][CH2:6][O:5][C:3]1=[O:4].[F:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[F:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH:2]2[CH2:7][CH2:6][O:5][C:3]2=[O:4])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 10796Cesium carbonateHCID 954632(3H)-Furanone, 3-bromodihydro-

Product 1

HCID 68859859HCID 68859859, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

α-Bromobutyrolactone (12.4 g, 0.075 mol) is added to a mixture of 4-fluorophenol (5.6 g, 0.05 mol) and caesium carbonate (17.9 g, 0.055 mol) in acetone (100 ml). The reaction medium is refluxed for two hours. After cooling to room temperature, the reaction is filtered through a bed of Celite and the filtrate is evaporated. The oily residue is purified by flash chromatography (1/2 EtOAc/heptane) to give the expected product in the form of an oil (9.8 g, 87%).

Workup

  1. temperatureThe reaction medium is refluxed for two hours
  2. filtrationthe reaction is filtered through a bed of Celite
  3. customthe filtrate is evaporated
  4. customThe oily residue is purified by flash chromatography (1/2 EtOAc/heptane)

Sources & evidence

ORD record
ord-a1813109bcae449ab53c27d02de8996c
Source dataset
uspto-grants-2009_02
Patent number
US07491747B2

Reaction notes

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