Methyl 4-bromobenzoate → 4-Bromobenzoic acid

HRID 906039Notes

Reaction equation

HRID 906039 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[CH:6][CH:5]=1>C1COCC1>[Br:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 12081Methyl 4-bromobenzoateHCID 14798Sodium Hydroxide

Product 1

HCID 114644-Bromobenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.1 eq of aqueous NaOH (1 M solution) was added to a solution of methyl 4-bromobenzoate in THF (0.5 M) and the reaction allowed to stir at RT overnight. THF was removed in vacuo and aqueous HCl (6M) was added dropwise to the basic solution at 0° C. to adjust the pH to pH 2. The resultant aqueous mixture was extracted with EtOAc (3×) and then the combined organics were washed with brine, dried over Na2SO4, filtered and the solvent evaporated in vacuo. The title compound was obtained in quantitative yield; MS (ES+) m/z 201 (M+H)+, m/z 203 (M+H)+

Workup

  1. customTHF was removed in vacuo and aqueous HCl (6M)
  2. additionwas added dropwise to the basic solution at 0° C.
  3. extractionThe resultant aqueous mixture was extracted with EtOAc (3×)
  4. washthe combined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-110bbf0fc335484b8ef4348e1f67f9de
Source dataset
uspto-grants-2011_09
Patent number
US08012982B2

Reaction notes

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