Water → 2-(3-Cyano-4-fluorophenyl)acetic acid

HRID 2173228Notes

Reaction equation

HRID 2173228 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]=C)=[CH:6][C:3]=1[C:4]#[N:5].I([O-])(=O)(=O)=[O:14].[Na+].[OH2:19]>C(Cl)(Cl)(Cl)Cl.C(#N)C.C(Cl)Cl.O.[Ru]=O>[C:4]([C:3]1[CH:6]=[C:7]([CH2:10][C:11]([OH:14])=[O:19])[CH:8]=[CH:9][C:2]=1[F:1])#[N:5]

Participants

8

Reactant 3

HCID 962Water2×HCID 23667635Sodium periodateHCID 247217702-Fluoro-5-(prop-2-en-1-yl)benzonitrile

Product 1

HCID 27739352-(3-Cyano-4-fluorophenyl)acetic acid

Reagents, catalysts & solvents 4

HCID 178526987HCID 178526987, compoundCatalystHCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 2-fluoro-5-(prop-2-en-1-yl)benzonitrile (1.9 g, 11.8 mmol) in CCl4 (25 mL), acetonitrile (25 mL) and water (38 mL) was added sodium periodate (8.83 g, 41.3 mmol) and ruthenium oxide hydrate (200 mg) and the resulting mixture was stirred at ambient temperature overnight. The mixture was diluted with 100 mL DCM and 100 mL of water. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified with silica gel column chromatography afford crude (3-cyano-4-fluorophenyl)acetic acid.

Workup

  1. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  2. concentrationconcentrated
  3. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-03de31c9935f4d4a9f35e42bcd69b928
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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