Chloroacetic Acid → 2-[2-(3-Fluorophenyl)ethoxy]acetic acid

HRID 2076815Notes

Reaction equation

HRID 2076815 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Cl[CH2:14][C:15]([OH:17])=[O:16]>CN(C=O)C.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][O:10][CH2:14][C:15]([OH:17])=[O:16])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 300Chloroacetic AcidHCID 24758Sodium hydrideHCID 5731322-(3-Fluorophenyl)ethanol

Product 1

HCID 247694442-[2-(3-Fluorophenyl)ethoxy]acetic acidYield 63.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(3-fluoro-phenyl)-ethanol (4.0 g, 28.5 mmol) in DMF (60 ml) was added sodium hydride (60% dispersion in oil, 2.40 g, 60 mmol). The suspension was heated to 60° C. for 0.75 hours before chloroacetic acid (4.72 g, 50 mmol) was added dropwise. After 36 hours at 60° C. the brown reaction mixture was brought to dryness under reduced pressure, dissolved in EtOAc and washed with 1M HCl, water and brine. The organic layers were dried (MgSO4), filtered, the solvent was removed under reduced pressure and the residue was purified by column chromatography (silica gel, EtOAc/heptane 3:1) to yield the title compound (2.02 g, 18 mmol; 36%) as colorless liquid. MS: m/e=197.4 [M−H]−.

Workup

  1. additionwas added dropwise
  2. washwashed with 1M HCl, water and brine
  3. dry with materialThe organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography (silica gel, EtOAc/heptane 3:1)

Sources & evidence

ORD record
ord-b0ecd2d840bb46eb80791d1973c825c5
Source dataset
uspto-grants-2011_04
Patent number
US07928106B2

Reaction notes

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