Hydrochloric Acid → 4-Bromo-2-nitrophenylacetic Acid

HRID 2096955Notes

Reaction equation

HRID 2096955 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9](C(OC)=O)[C:10]([O:12]C)=[O:11])=[C:5]([N+:18]([O-:20])=[O:19])[CH:4]=1.O>CS(C)=O>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[C:5]([N+:18]([O-:20])=[O:19])[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 157405961,3-Dimethyl 2-(4-bromo-2-nitrophenyl)propanedioate

Product 1

HCID 2715514-Bromo-2-nitrophenylacetic AcidYield 94%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

6M Aqueous hydrochloric acid (200 mL) was added to a stirred solution of dimethyl 2-(4-bromo-2-nitrophenyl)malonate (preparation 1a, 55.45 g, 170 mmol) in dimethylsulphoxide (250 mL) at room temperature and then mixture was warmed to 130° C. with stirring. After 5 hours, the mixture was cooled and water (400 mL) was added with stirring and the mixture was left to cool overnight. The precipitate was filtered, washed with water and dried in vacuo to give the title compound (41.0 g, 94%) as a white solid.

Workup

  1. temperaturethe mixture was cooled
  2. stirringwith stirring
  3. waitthe mixture was left
  4. temperatureto cool overnight
  5. filtrationThe precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-441051af1e704301934b8c68cc20e0a2
Source dataset
uspto-grants-2013_05
Patent number
US08450341B2

Reaction notes

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