Sodium Hydroxide → 2-(3-Bromo-5-chlorophenyl)acetic acid

HRID 563679Notes

Reaction equation

HRID 563679 reaction equation
C[O:2][C:3](=[O:17])[CH:4]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Br:16])[CH:10]=1)C(OC)=O.[OH-].[Na+]>CO>[Br:16][C:11]1[CH:10]=[C:9]([CH2:4][C:3]([OH:17])=[O:2])[CH:14]=[C:13]([Cl:15])[CH:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 574588062-(3-Bromo-5-chloro-phenyl)-malonic acid dimethyl ester

Product 1

HCID 153652222-(3-Bromo-5-chlorophenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(3-Bromo-5-chloro-phenyl)-malonic acid dimethyl ester (19 g, 59 mmol) in MeOH (500 mL) was treated with 1N aqueous NaOH (237 mL, 237 mmol) at 50° C. for 1.5 hours. The mixture was concentrated, and the residue was acidified and extracted twice with EtOAc. The combined organic layers were dried, filtered, and concentrated to give the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted twice with EtOAc
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-76950616128c4596bd4da0efc3e770ac
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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