Water → HCID 22398645, compound

HRID 916035Notes

Reaction equation

HRID 916035 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].[Na+].[Cl-].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 NaCl in 40 mL of DMSO with 2 mL of water was warmed at 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
  2. temperatureat reflux
  3. customGas evolution was clearly evident early in the reaction
  4. temperaturethe reaction was cooled
  5. extractionextracted with four 75 mL portions of EtOAc
  6. washThe combined organic layers were washed with six 50 mL portions of brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford an oil which
  11. customThe tan solid was triturated with hexanes
  12. filtrationcollected by filtration

Sources & evidence

ORD record
ord-c7227203acc64e969a0efabd06d83282
Source dataset
uspto-grants-2007_09
Patent number
US07268152B2

Reaction notes

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