Water → HCID 22398645, compound

HRID 1988179Notes

Reaction equation

HRID 1988179 reaction equation
COC(=O)[CH:4]([C:17]#[N:18])[C:5]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[O:15][CH3:16])([CH3:7])[CH3:6].[Cl-].[Na+].O>CS(C)=O.[Cl-].[Na+].O>[F:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]([CH3:6])([CH3:7])[CH2:4][C:17]#[N:18])=[C:9]([O:15][CH3:16])[CH:10]=1

Participants

6

Reactant 3

HCID 962WaterHCID 5234Sodium ChlorideHCID 20796144HCID 20796144, compound

Product 1

HCID 22398645HCID 22398645, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 4.2 g (15.03 mmol) of 2-cyano-3-(4-fluoro-2-methoxyphenyl)-3-methylbutyric acid methyl ester and 2.5 g (42.77 mmol) of sodium chloride in 40 mL of DMSO with 2 mL of water was warmed to reflux. Gas evolution was clearly evident early in the reaction. After 4 hours, the reaction was cooled and diluted with 100 mL of brine and extracted with four 75 mL portions of EtOAc. The combined organic layers were washed with six 50 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated to afford an oil which solidified under vacuum. The tan solid was triturated with hexanes and collected by filtration to afford 2.52 g (81%) of 3-(4-fluoro-2-methoxyphenyl)-3-methylbutyronitrile, m.p. 80° C.-83° C.

Workup

  1. temperaturewas warmed to reflux
  2. customGas evolution was clearly evident early in the reaction
  3. temperaturethe reaction was cooled
  4. extractionextracted with four 75 mL portions of EtOAc
  5. washThe combined organic layers were washed with six 50 mL portions of brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford an oil which
  10. customThe tan solid was triturated with hexanes
  11. filtrationcollected by filtration

Sources & evidence

ORD record
ord-c8f08708766e4f2ea40398ebf6abe645
Source dataset
uspto-grants-2009_06
Patent number
US07553966B2

Reaction notes

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