2-(4-Chlorophenyl)-1-(3,4-difluoro-2-hydroxy-phenyl)-4-methyl-pentane-1,3-dione → HCID 68704522, compound

HRID 14460Notes

Reaction equation

HRID 14460 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[C:12]=2O)=[O:10])=[CH:4][CH:3]=1>C(O)(=O)C.Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9](=[O:10])[C:11]3[C:12](=[C:13]([F:18])[C:14]([F:17])=[CH:15][CH:16]=3)[O:24][C:20]=2[CH:21]([CH3:23])[CH3:22])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 686997002-(4-Chlorophenyl)-1-(3,4-difluoro-2-hydroxy-phenyl)-4-methyl-pentane-1,3-dione

Product 1

HCID 68704522HCID 68704522, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-(4-chlorophenyl)-1-(3,4-difluoro-2-hydroxy-phenyl)-4-methyl-pentane-1,3-dione (3.65 g, 10.3 mmol) in acetic acid (36 ml) and concentrated HCl solution (2 ml) is stirred at 140° C. for 3 h. The reaction mixture is cooled to room temperature, poured onto ice-water and extracted with methylene chloride. The organic layer is washed with saturated sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and evaporated to dryness in vacuo to afford the title compound as a brown solid.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. additionpoured onto ice-water
  3. extractionextracted with methylene chloride
  4. washThe organic layer is washed with saturated sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-fa224b4cc0cd49ce92d0db54d17f8641
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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