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

HRID 2100502Notes

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

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-(3-fluoro-phenyl)-ethanol (4.0 g, 28.5 mmol) in DMF (60 ml) was added a 60% dispersion of sodium hydride in oil (2.40 g, 60 mmol). The suspension was heated to 60° C. for 0.75 hours. 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 over MgSO4, filtrated, the solvent was removed under reduced pressure and the residue purified by column chromatography (silica gel, EtOAc/heptane, 3/1) to yield [2-(3-fluoro-phenyl)-ethoxy]-acetic acid (2.02 g, 18 mmol; 36%) as colorless liquid. MS (m/e): 197.4 [M−H]−.

Workup

washwashed with 1M HCl, water and brine
dry with materialThe organic layers were dried over MgSO4
filtrationfiltrated
customthe solvent was removed under reduced pressure
customthe residue purified by column chromatography (silica gel, EtOAc/heptane, 3/1)

Sources & evidence

ORD record: ord-8e4fd372f6b64ded9ccd157e3a1c104d
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572801B2

Reaction notes

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