Water → Ethyl 4-(3-fluoro-phenoxy)butanoate

HRID 56250Notes

Reaction equation

HRID 56250 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Br[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 97433-FluorophenolHCID 10796Cesium carbonateHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 21812847Ethyl 4-(3-fluoro-phenoxy)butanoateYield 99.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-fluorophenol (6.00 g, 53.5 mmol), ethyl 4-bromobutanoate (15.70 g, 80.5 mmol) and Cs2CO3 (26.20 g, 80.4 mmol) in DMF (25 mL) under N2 was refluxed overnight. The mixture was then cooled to rt and 150 mL of water was added. The resulting mixture was extracted with DCM (100 mL×2) and the combined organic phases were washed with brine (100 mL×2), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=10:1) to give the title compound as colorless oil (12.0 g, 99%).

Workup

  1. temperaturewas refluxed overnight
  2. extractionThe resulting mixture was extracted with DCM (100 mL×2)
  3. washthe combined organic phases were washed with brine (100 mL×2)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=10:1)

Sources & evidence

ORD record
ord-9b6b257fbd8b489aa07d78708df4c121
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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