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Water → 1,3-Propanedione, 1,3-bis(4-fluorophenyl)-

HRID 68558
Notes
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Reaction equation

HRID 68558 reaction equation
CC([O-])(C)C.[K+].[CH3:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)=[O:9].C[O:18][C:19](=O)[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1.O>C1COCC1>[F:16][C:13]1[CH:14]=[CH:15][C:10]([C:8](=[O:9])[CH2:7][C:19]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[O:18])=[CH:11][CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 98284'-FluoroacetophenoneHCID 67878Methyl 4-fluorobenzoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 738961,3-Propanedione, 1,3-bis(4-fluorophenyl)-

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent

Procedure

9.27 g KOtBu was added to 109 mg 18-Krone-6 and 5 mL 4-fluoracetophenone in 150 mL THF. After 30 min at RT 10.7 g 4-fluoro-benzoic acid methyl ester was added and stirred for 3 h at RT. The reaction was decomposed with water and filtered, the filtrate was concentrated and the residue was purified by chromatography on silica gel (cyclohexane/EE: 98:2). The solvent was removed and 3.9 g of the desired compound was obtained.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by chromatography on silica gel (cyclohexane/EE: 98:2)
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-70cfdcee53bf4b3191c40dab3dfbd6eb
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822464B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes