Hydrochloric Acid → 2-(3-BROMOPHENYL)-2-OXOACETIC ACID

HRID 886591Notes

Reaction equation

HRID 886591 reaction equation
C([O:3][C:4](=[O:14])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[CH:8]=1)=[O:6])C.[OH-].[K+].Cl>CO>[Br:13][C:9]1[CH:8]=[C:7]([C:5](=[O:6])[C:4]([OH:14])=[O:3])[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 12252915ethyl 2-(3-bromophenyl)-2-oxoacetate

Product 1

HCID 122529142-(3-BROMOPHENYL)-2-OXOACETIC ACIDYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (3-Bromo-phenyl)-oxo-acetic acid ethyl ester (1 g, 3.9 mmol) in methanol (10 mL) was added potassium hydroxide (2 mL, 50% w/v in water) and the resulting mixture was stirred at room temperature for 30 minutes. Hydrochloric acid (1 N) was added to adjust to pH 4. The mixture was extracted with ethyl acetate (5 mL×4) and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was used in next step without further purification (0.8 g, 89% yield). MS: m/z 230 (M−H+).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (5 mL×4)
  2. dry with materialthe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was used in next step without further purification (0.8 g, 89% yield)

Sources & evidence

ORD record
ord-8d77c460a6724828957e1ec7db76c1ba
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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