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

HRID 51627Notes

Reaction equation

HRID 51627 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-e72afff758084c90960114a76fc39878
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Reaction notes

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