Water → 2-(5-Bromo-2-chlorophenyl)acetic acid

HRID 1625882Notes

Reaction equation

HRID 1625882 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH2:8][C:9]#N)[CH:7]=1.S(=O)(=O)(O)[OH:13].[OH2:17]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH2:8][C:9]([OH:13])=[O:17])[CH:7]=1

Participants

4

Reactant 3

HCID 962Water2×HCID 1118Sulfuric AcidHCID 534291382-(5-Bromo-2-chlorophenyl)acetonitrile

Product 1

HCID 155124412-(5-Bromo-2-chlorophenyl)acetic acid

Conditions

Temperature
160 °C

Procedure

The above 5-bromo-2-chlorophenylacetonitrile was added to water (90 ml)-sulfuric acid (75 ml), and the mixture was stirred under heating at 160° C. overnight. The mixture was further diluted with water, and cooled to 0° C. The solvent was removed by decant, and the residue was dissolved in diethyl ether. The solution was washed with water and brine, and extracted with 10% sodium hydroxide. To the extract was added concentrated hydrochloric acid to make the solution acidic. The precipitates were collected by filtration, and purified by silica gel column chromatography (chloroform) to give 5-bromo-2-chlorophenylacetic acid (6.67 g) as colorless crystals. ESI-Mass m/Z 247/249 (M−H).

Workup

  1. temperaturecooled to 0° C
  2. customThe solvent was removed
  3. customby decant
  4. dissolutionthe residue was dissolved in diethyl ether
  5. washThe solution was washed with water and brine
  6. extractionextracted with 10% sodium hydroxide
  7. additionTo the extract was added concentrated hydrochloric acid
  8. filtrationThe precipitates were collected by filtration
  9. custompurified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-ecd69afe223b45d485e458169540a478
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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