Potassium Carbonate → 1-(p-Chlorophenyl)-1-cyclopropyl-2-fluoro-4-(4-fluoro-3-phenoxyphenyl)-1,3-butadiene

HRID 479888Notes

Reaction equation

HRID 479888 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH:11]2[CH2:13][CH2:12]2)=[C:7]([F:10])[CH:8]=O)=[CH:4][CH:3]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23]S(F)(=O)=O)=[CH:19][C:18]=1[O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C1OCCOCCOCCOCCOCCOC1>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH:11]2[CH2:13][CH2:12]2)=[C:7]([F:10])[CH:8]=[CH:23][C:20]2[CH:21]=[CH:22][C:17]([F:16])=[C:18]([O:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:19]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12113197(4-Fluoro-3-phenoxyphenyl)methanesulfonyl fluorideHCID 540115002-Fluoro-3-cyclopropyl-3-(p-chlorophenyl)acrylaldehyde

Product 1

HCID 540353111-(p-Chlorophenyl)-1-cyclopropyl-2-fluoro-4-(4-fluoro-3-phenoxyphenyl)-1,3-butadieneYield 93%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of p-chloro-β-cyclopropyl-α-fluoro-cinnamaldehyde (224.6 mg, 1 mmol), (4-fluoro-3-phenoxyphenyl)methanesulfonyl fluoride (312.7 mg, 1.1 mmol), potassium carbonate (552.8 mg, 4 mmol), and 18-crown-6 (13.2 mg, 0.05 mmol) in acetonitrile is stirred at room temperature overnight, quenched with water, and extracted with ethyl acetate. The organic extract is washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the title product (380 mg, 94% pure by GC analysis, 93% yield) which is identified by 1H and 19F NMR spectral analyses.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washis washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2ef5e20f99904fe7b863639e5de3628e
Source dataset
uspto-grants-2003_11
Patent number
US06646166B1

Reaction notes

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