Dimethylformamide → 5-Chloro-4-hydroxymethylthiophene-2-carbonitrile

HRID 34072노트

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HRID 34072 반응식
Br[C:2]1[S:6][C:5]([Cl:7])=[C:4]([CH2:8][OH:9])[CH:3]=1.[CH3:10][N:11](C)C=O>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:7][C:5]1[S:6][C:2]([C:10]#[N:11])=[CH:3][C:4]=1[CH2:8][OH:9]

참가 물질

6

반응물 2

HCID 6228DimethylformamideHCID 23070160(5-Bromo-2-chlorothiophen-3-yl)methanol

생성물 1

HCID 230701655-Chloro-4-hydroxymethylthiophene-2-carbonitrile

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

To a solution of 25.0 g (5-bromo-2-chlorothiophen-3-yl)methanol in 330 mL of dimethylformamide, 25.8 g of zinc cyanide (I) and 12.7 g tetrakis(triphenylphosphine)palladium(0) were added at room temperature, and stirred at 100° C. for 4 hours. Diluting with ethyl acetate, the organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-1:5), to afford 16.0 g of the title compound as colorless crystals.

후처리

  1. washthe organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customThe crude product was purified
  5. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-1:5)

출처 및 근거

ORD 기록
ord-fe53eddbf6e24573b0d61b6749f23191
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429609B2

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