Water → 4-Bromo-2-chloro-5-(trifluoromethoxy)benzoic acid

HRID 1504330Notes

Reaction equation

HRID 1504330 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([O:10][C:11]([F:14])([F:13])[F:12])[C:7]([Br:15])=[CH:6][C:5]=1[Cl:16].O.[OH-].[Li+]>CO>[Br:15][C:7]1[C:8]([O:10][C:11]([F:12])([F:13])[F:14])=[CH:9][C:4]([C:3]([OH:17])=[O:2])=[C:5]([Cl:16])[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 86682803HCID 86682803, compound

Product 1

HCID 866828054-Bromo-2-chloro-5-(trifluoromethoxy)benzoic acidYield 100.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 4-bromo-2-chloro-5-trifluoromethoxy-benzoic acid methyl ester (1.0 g, 3.0 mmol, Preparation 48) dissolved in methanol (4 mL) and water (4 mL) was added lithium hydroxide (360 mg, 15 mmol). The reaction mixture was stirred at 60° C. for 1 h and concentrated. The reaction mixture was adjusted to acidic pH with 1 N HCl, dissolved in EtOAc (60 mL) and washed with water (60 mL). The aqueous layer was extracted with EtOAc (60 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated to produce the title intermediate (966 mg, 100% yield) as a white powder.

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in EtOAc (60 mL)
  3. washwashed with water (60 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (60 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-09a9b6bceccd46d68439d05de89c2d39
Source dataset
uspto-grants-2015_12
Patent number
US09212168B2

Reaction notes

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