Water → 2-(2-Fluoro-4-iodophenyl)acetic acid

HRID 841311Notes

Reaction equation

HRID 841311 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]#N.[OH2:12].[OH-:13].[K+]>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 222405322-(2-Fluoro-4-iodophenyl)acetonitrile2×

Product 1

HCID 222403932-(2-Fluoro-4-iodophenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-fluoro-4-iodo-phenyl acetonitrile (Intermediate 2, 2.05 g, 7.83 mmol) in ethanol (50 mL and water (15 mL) was treated with potassium hydroxide (3.4 g, 60.7 mmol) and refluxed for 4 h. The volatiles were distilled off in vacuo and the residue was diluted with water and poured into cold, dilute hydrochloric acid and the precipitated solid was filtered. The solid was dissolved in diethyl ether, and the organic solution was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title compound a pale yellow solid (1.75 g, 79%).

Workup

  1. temperaturerefluxed for 4 h
  2. distillationThe volatiles were distilled off in vacuo
  3. additionthe residue was diluted with water
  4. additionpoured into cold, dilute hydrochloric acid
  5. filtrationthe precipitated solid was filtered
  6. dissolutionThe solid was dissolved in diethyl ether
  7. dry with materialthe organic solution was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-99878e57e9bb40f9b0bf1c6ea6ed30ae
Source dataset
uspto-grants-2002_04
Patent number
US06369225B1

Reaction notes

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