3-(3,5-Difluorophenyl)pentanedioic acid → HCID 15896148, compound

HRID 1954928Notes

Reaction equation

HRID 1954928 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:14][C:15]([OH:17])=O)[CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1>CO.ClCCl>[F:8][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[C:4]2[C:5]=1[C:15](=[O:17])[CH2:14][CH:9]2[CH2:10][C:11]([OH:13])=[O:12]

Participants

3

Reactant 1

HCID 158961473-(3,5-Difluorophenyl)pentanedioic acid

Product 1

HCID 15896148HCID 15896148, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

This compound was prepared in an analogous manner to that of Example 25d with the replacement of 3-(3-fluorophenyl)glutaric acid with 3-(3,5-difluorophenyl)glutaric acid (9.02 g, 36.9 mmol) and an increase of the heating time from 10 min to 30 min. Chromatography of the collected product on a column of Silica Gel 60 (51×450 mm) with methanol:dichloromethane (4:96) gave a material which was recrystallized from water to give 1.93 g (23%) of 2-(4,6-difluoro-3-oxo-1-indanyl)acetic acid: m.p., 170-172° C.;

Workup

  1. temperaturean increase of the heating time from 10 min to 30 min
  2. customwas recrystallized from water

Sources & evidence

ORD record
ord-41e695514f044fef890fd6aa4208ca9a
Source dataset
uspto-grants-2000_09
Patent number
US06124284

Reaction notes

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