Hydrochloric Acid → 5-Bromo-2-chloro-3-methoxybenzoic acid

HRID 576329Notes

Reaction equation

HRID 576329 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:13][CH3:14])[C:5]([Cl:12])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+].Cl>C1COCC1.O.CO>[Br:1][C:2]1[CH:3]=[C:4]([O:13][CH3:14])[C:5]([Cl:12])=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58801718Methyl 5-bromo-2-chloro-3-methoxybenzoate

Product 1

HCID 710769615-Bromo-2-chloro-3-methoxybenzoic acidYield 96%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 55 (25.0 g, 89.4 mmol) in THF (100 mL), H2O (100 mL) and MeOH (100 mL) was added aq. 5 N NaOH dropwise at 0° C. The mixture was stirred at room temperature for 1 hour. Conc. HCl was added to the mixture to acidify and the mixture was extracted with EtOAc (500 mL×2). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to afford the crude acid 56 (22.6 g, 96%) as an orange solid.

Workup

  1. extractionthe mixture was extracted with EtOAc (500 mL×2)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1d5fc1582be94d5fab78cac3a18486f4
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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