4-Fluorophenol → 3-[2-(4-Fluoro-phenoxy)-6-trifluoromethyl-pyridin-3-yl]-acrylic acid

HRID 2266003Notes

Reaction equation

HRID 2266003 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:12]1[C:17]([CH:18]=[CH:19][C:20]([OH:22])=[O:21])=[CH:16][CH:15]=[C:14]([C:23]([F:26])([F:25])[F:24])[N:13]=1>CN(C=O)C.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:12]2[C:17]([CH:18]=[CH:19][C:20]([OH:22])=[O:21])=[CH:16][CH:15]=[C:14]([C:23]([F:24])([F:26])[F:25])[N:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 97324-FluorophenolHCID 24758Sodium hydrideHCID 723356323-(2-Chloro-6-trifluoromethyl-pyridin-3-yl)-acrylic acid

Product 1

HCID 687828813-[2-(4-Fluoro-phenoxy)-6-trifluoromethyl-pyridin-3-yl]-acrylic acidYield 33.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Fluoro-phenol (116 mg, 1.03 mmol) and sodium hydride (53 mg, 1.3 mmol) were added in DMF (7 mL). The reaction mixture was stirred for 10 mins and then 3-(2-chloro-6-trifluoromethyl-pyridin-3-yl)-acrylic acid (132 mg, 0.52 mmol) was added into the reaction mixture. The reaction mixture was diluted with EtOAc, and washed with water and brine. The organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The resulting residue was purified by column chromatography (Hex EtOAc=1/1) to give the title product (57 mg).

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by column chromatography (Hex EtOAc=1/1)

Sources & evidence

ORD record
ord-709466a3b14848f98e920ac37cea6715
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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