4'-Fluoroacetophenone → Methyl [2-[4-(4-acetylphenoxy)phenyl]-4-(2-chlorophenyl)thien-3-yl]acetate

HRID 2373706Notes

Reaction equation

HRID 2373706 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[S:11][CH:12]=1.F[C:26]1[CH:31]=[CH:30][C:29]([C:32](=[O:34])[CH3:33])=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O>[C:32]([C:29]1[CH:30]=[CH:31][C:26]([O:19][C:16]2[CH:17]=[CH:18][C:13]([C:10]3[S:11][CH:12]=[C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[C:9]=3[CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:14][CH:15]=2)=[CH:27][CH:28]=1)(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 98284'-FluoroacetophenoneHCID 11430Potassium CarbonateHCID 86607176Methyl [4-(2-chlorophenyl)-2-(4-hydroxyphenyl)thien-3-yl]acetate

Product 1

HCID 86607179Methyl [2-[4-(4-acetylphenoxy)phenyl]-4-(2-chlorophenyl)thien-3-yl]acetateYield 61.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution containing methyl [4-(2-chlorophenyl)-2-(4-hydroxyphenyl)thien-3-yl]acetate (0.50 g, 1.40 mmol) and 4′-fluoroacetophenone (0.195 g, 1.40 mmol) in DMA (5 mL) was added K2CO3 (0.211 g, 1.53 mmol). The solution was heated to reflux overnight. The solvent was removed and the resulting solid was partitioned between CHCl3 and H2O. The CHCl3 was dried (MgSO4) and the solvent removed to yield methyl [2-[4-(4-acetylphenoxy)phenyl]-4-(2-chlorophenyl)thien-3-yl]acetate (0.41 g) as a white solid.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux overnight
  3. customThe solvent was removed
  4. customthe resulting solid was partitioned between CHCl3 and H2O
  5. dry with materialThe CHCl3 was dried (MgSO4)
  6. customthe solvent removed

Sources & evidence

ORD record
ord-7262619f53c54c12882b2bb568a4fc16
Source dataset
uspto-grants-2008_12
Patent number
US07459567B2

Reaction notes

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