Trimethylsilyl cyanide → HCID 53403951, compound

HRID 336825Notes

Reaction equation

HRID 336825 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[F:12])=[O:4].C[Si]([C:17]#[N:18])(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(#N)C.[Cl-].[Na+]>[F:12][C:6]1[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:5]=1[C:3](=[O:4])[CH2:2][C:17]#[N:18]

Participants

6

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 2724141Tetrabutylammonium FluorideHCID 22313787HCID 22313787, compound

Product 1

HCID 53403951HCID 53403951, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2.5 g (10.73 mmol) of 2-bromo-1-(2-fluoro-4-hydroxyphenyl)ethanone in 100 ml of acetonitrile are respectively added 1.2 g (11.8 mmol) of trimethylsilyl cyanide and 12.3 ml (12.3 mmol) of tetrabutyl-ammonium fluoride solution (1M in THF). The reaction mixture is stirred at room temperature for 16 h then diluted with an aqueous solution saturated with sodium chloride. The product is extracted several times with ethyl acetate. The organic phases are combined, dried over magnesium sulfate, filtered, then evaporated. The residue is purified by chromatography on silica (cyclohexane/ethyl acetate eluent: 5:5) to give 1.2 g (62%) of 3-(2-fluoro-4-hydroxyphenyl)-3-oxopropanenitrile in the form of a yellow solid.

Workup

  1. extractionThe product is extracted several times with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is purified by chromatography on silica (cyclohexane/ethyl acetate eluent: 5:5)

Sources & evidence

ORD record
ord-1eb2817b5b214bbdb5573717dbb5971b
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Reaction notes

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