Potassium Hydroxide → (2-Bromo-4-nitrophenyl)acetic acid

HRID 2173391Notes

Reaction equation

HRID 2173391 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH:11](C(OCC)=O)[C:12]([O:14]CC)=[O:13].[OH-].[K+]>CO.O>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][C:12]([OH:14])=[O:13]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86693027HCID 86693027, compound

Product 1

HCID 12404388(2-Bromo-4-nitrophenyl)acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A solution of diethyl (2-bromo-4-nitrophenyl)propanedioate (5.6 g, 17 mmol) in 120 mL of methanol and 100 mL of water was added KOH (2.8 g, 50 mmol), and the mixture was heated to 70° C. for 3.5 hours. The reaction was cooled to ambient temperature, distilled off methanol under reduce pressure and adjusted pH to 2 with conc. HCl. Extracted with EtOAc and the organic layers were washed with water, brine and dried over anhydrous sodium sulfate, concentrated to get (2-bromo-4-nitrophenyl)acetic acid. 1H-NMR (300 MHz, CDCl3) δ ppm 8.39 (s, 1H), 8.07˜8.11 (m, 1H), 7.43 (d, J=8.3 Hz, 1H), 3.88 (s, 2H).

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. distillationdistilled off methanol
  3. extractionExtracted with EtOAc
  4. washthe organic layers were washed with water, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9989f54755a64b23bd8b3a32cf3c1a28
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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