Trimethylsilyl cyanide → HCID 53403951, 화합물

HRID 336825노트

반응식

HRID 336825 반응식
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]

참가 물질

6

반응물 3

HCID 82115Trimethylsilyl cyanideHCID 2724141Tetrabutylammonium FluorideHCID 223137872-Bromo-1-(2-fluoro-4-hydroxyphenyl)ethanone

생성물 1

HCID 53403951HCID 53403951, 화합물수율 62.4%

시약·촉매·용매 2

HCID 5234Sodium Chloride용매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1eb2817b5b214bbdb5573717dbb5971b
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889711B2

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