Hydrochloric Acid → 4-Bromo-2-methoxybenzoic acid

HRID 2035677Notes

Reaction equation

HRID 2035677 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.[OH-].[K+].Cl.O>CO>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 15128242Methyl 4-bromo-2-methoxybenzoate

Product 1

HCID 134507554-Bromo-2-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A solution of methyl 4-bromo-2-methoxybenzoate (1 g, 4.08 mmol) in 20 ml of MeOH was treated with 4.08 ml of a 2 N solution of potassium hydroxide and refluxed at 65° C. for 2.5 hours. MeOH was removed in vacuo and the remaining water was taken-up in 100 ml of EtOAc and quenched with 30 ml of 1 N HCl (3.5 eq.) and 100 ml of water. Layers were separated and the aqueous layer was extracted twice with EtOAc. Organics were combined, dried over sodium sulfate, and concentrated under reduced pressure to a yellow-white solid (950.7 mg crude).

Workup

  1. customMeOH was removed in vacuo
  2. customLayers were separated
  3. extractionthe aqueous layer was extracted twice with EtOAc
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure to a yellow-white solid (950.7 mg crude)

Sources & evidence

ORD record
ord-118249233c2e4a899d120f3cdc9bbcbe
Source dataset
uspto-grants-2013_11
Patent number
US08575150B2

Reaction notes

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