HCID 53628956, compound → 3-(4-bromophenyl)pentanedioic Acid

HRID 1784714Notes

Reaction equation

HRID 1784714 reaction equation
C([O:3][C:4](=[O:30])[CH:5](C(OCC)=O)[CH:6]([C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=1)[CH:7](C(OCC)=O)[C:8]([O:10]CC)=[O:9])C>Cl.C(O)(=O)C>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([CH:6]([CH2:7][C:8]([OH:10])=[O:9])[CH2:5][C:4]([OH:30])=[O:3])=[CH:19][CH:20]=1

Participants

4

Reactant 1

HCID 53628956HCID 53628956, compound

Product 1

HCID 106846833-(4-bromophenyl)pentanedioic Acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of 3-(4-bromo-phenyl)-2,4-bis-ethoxycarbonyl-pentanedioic acid diethyl ester in concentrated hydrochloric acid (100 ml) and acetic acid (100 ml) was refluxed for 8 h. Removal of the solvent in vacuo and recrystallization of the residue from acetonitrile yielded 3-(4-bromo-phenyl)-pentanedioic acid (22.84 g in 1st crop, 65%, 3.84 g in 2nd crop, 11.05% from 4-bromobenzaldehyde).

Workup

  1. customRemoval of the solvent
  2. customin vacuo and recrystallization of the residue from acetonitrile

Sources & evidence

ORD record
ord-4f849f56ce6d459792352a6feaaeea00
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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