Hydrochloric Acid → 4-Bromo-2-cyanobenzoic acid

HRID 2411196Notes

Reaction equation

HRID 2411196 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[C:4]([C:12]#[N:13])[CH:3]=1.[OH-].[Li+].Cl>C(COC)OC.O.[Cl-].[Na+].O>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[C:4]([C:12]#[N:13])[CH:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58484706Methyl 4-bromo-2-cyanobenzoate

Product 1

HCID 584845854-Bromo-2-cyanobenzoic acidYield 99.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Methyl 4-bromo-2-cyanobenzoate (8.53 g) described in Preparation Example 75 was dissolved in dimethoxyethane (140 mL), a solution of lithium hydroxide 1 hydrate (2.24 g) in water (54 mL) was added dropwise under ice-cooling, and the mixture was stirred at the same temperature for 30 min. To the reaction mixture was added dropwise 1N hydrochloric acid (60 mL) under ice-cooling, saturated brine was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and the solvent was evaporated to give the title compound (7.97 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b74320ece85a4a7c8a81de8d1d8c4f90
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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