Hydrochloric Acid → 2-(3-Bromo-5-chlorophenyl)propanoic acid

HRID 1810583Notes

Reaction equation

HRID 1810583 reaction equation
C([O:3][C:4](=[O:15])[CH:5]([C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[C:9]([Br:14])[CH:8]=1)[CH3:6])C.CO.[Li+].[OH-].Cl>O.C1COCC1>[Br:14][C:9]1[CH:8]=[C:7]([CH:5]([CH3:6])[C:4]([OH:15])=[O:3])[CH:12]=[C:11]([Cl:13])[CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 574588072-(3-Bromo-5-chloro-phenyl)-propionic acid ethyl ester

Product 1

HCID 574588082-(3-Bromo-5-chlorophenyl)propanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(3-Bromo-5-chloro-phenyl)-propionic acid ethyl ester (2.0 g, 6.9 mmol) in 2:2:1 MeOH:THF:H2O was treated with 1N aqueous LiOH (3 mL) and stirred at room temperature overnight. The mixture was acidified with 10% aqueous HCl (10 mL) and extracted three times with EtOAc. The combined organic layers were concentrated, and the residue was purified by silica gel chromatography to give the title compound.

Workup

  1. extractionextracted three times with EtOAc
  2. concentrationThe combined organic layers were concentrated
  3. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-599c298e55234cdda993562fd6b1f280
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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