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Sodium Cyanide → HCID 53434575, 화합물

HRID 2240935
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HRID 2240935 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:22])=[C:6]([CH2:8][CH2:9][CH2:10]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:7]=1.[C-:23]#[N:24].[Na+]>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:22])=[C:6]([CH2:8][CH2:9][CH2:10][C:23]#[N:24])[CH:7]=1
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참가 물질

4

반응물 2

HCID 8929Sodium CyanideHCID 59305329HCID 59305329, 화합물

생성물 1

HCID 53434575HCID 53434575, 화합물수율 101.9%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
80 °C

실험 절차

A solution of Toluene-4-sulfonic acid 3-(5-bromo-2-fluoro-phenyl)-propyl ester (0.59 g, 1.5 mmol) in anhydrous DMSO (3.0 mL) was added sodium cyanide (0.112 g, 2.3 mmol) and heated to 80° C. for 12 h. The mixture was cooled and partitioned between ethyl acetate and H2O, and the aqueous layer was extracted with ethyl acetate (15 mL). The combined organic layers were washed with brine (1×15 mL), dried (MgSO4), filtered and concentrated under reduced pressure. Silica gel chromatography (10-20% Ethyl acetate/petroleum ether) gave the title compound as a clear oil (0.37 g, 99%), and was used directly in the next step.

후처리

  1. temperatureThe mixture was cooled
  2. custompartitioned between ethyl acetate and H2O
  3. extractionthe aqueous layer was extracted with ethyl acetate (15 mL)
  4. washThe combined organic layers were washed with brine (1×15 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-422ed9bc8935452eb224d62d382e23d9
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07723368B2

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