Potassium Carbonate → 2-(4-Fluoro-3-methyl-phenoxy)-hexanoic acid methyl ester

HRID 1361049Notes

Reaction equation

HRID 1361049 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH:4](Br)[CH2:5][CH2:6][CH2:7][CH3:8].[F:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=1[CH3:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:10])[CH:4]([O:18][C:15]1[CH:16]=[CH:17][C:12]([F:11])=[C:13]([CH3:19])[CH:14]=1)[CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 95578Hexanoic acid, 2-bromo-, methyl esterHCID 27373944-Fluoro-3-methylphenol

Product 1

HCID 597751852-(4-Fluoro-3-methyl-phenoxy)-hexanoic acid methyl esterYield 76.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromo-hexanoic acid methyl ester (0.500 g, 2.404 mmol) and 4-fluoro-3-methylphenol (0.303 g, 2.404 mmol) in 15 mL of DMF, was added K2CO3 (1.661 g, 12.020 mmol). After stirring at room temperature under N2 for 88 h, the reaction mixture was diluted with 60 mL of water and extracted with dichloromethane (60 mL×3). The organic extracts were combined and dried over anhydrous Na2SO4. After removing the solvent under reduced pressure, the product was isolated by Flash chromatography (silica gel) eluting with 0-20% ethyl acetate/hexanes to give the title compound as yellow oil (0.467 g, 76% yield). LC-MS: tR=10.5 min; m/z 255 (M+H)+.

Workup

  1. extractionextracted with dichloromethane (60 mL×3)
  2. dry with materialdried over anhydrous Na2SO4
  3. customAfter removing the solvent under reduced pressure
  4. customthe product was isolated by Flash chromatography (silica gel)
  5. washeluting with 0-20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-bbcc6eb5f8ad40e4b640f7efd6e964d9
Source dataset
uspto-grants-2011_02
Patent number
US07879911B2

Reaction notes

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