Sodium Cyanide → [1-(4-Bromophenyl)-cyclopentyl]-acetonitrile

HRID 2169270노트

반응식

HRID 2169270 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:13]OS(C)(=O)=O)[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C-:19]#[N:20].[Na+]>CS(C)=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:13][C:19]#[N:20])[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 8929Sodium CyanideHCID 86725919Methanesulfonic acid 1-(4-bromophenyl)-cyclopentylmethyl ester

생성물 1

HCID 86725920[1-(4-Bromophenyl)-cyclopentyl]-acetonitrile수율 87.7%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

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온도
140 °C

실험 절차

To a stirred solution of methanesulfonic acid 1-(4-bromophenyl)-cyclopentylmethyl ester (227) (20 g, 60.01 mmol) in dimethyl sulfoxide (100 mL) were added KI (0.99 g, 6.00 mmol) and NaCN (4.41 g, 90.02 mmol). The reaction mixture was then stirred at 140° C. for 5 h. After completion of the reaction, the reaction mixture was diluted with water, extracted with ethyl acetate (2×250 mL) and the organic layer was washed with water and brine. It was then dried over Na2SO4, and concentrated. The crude product was purified by 100-200 silica column chromatography using 5% ethyl acetate in hexane as the eluent to give [1-(4-bromophenyl)-cyclopentyl]-acetonitrile (228) (13.9 g, 87%) as a colorless thick liquid.

후처리

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (2×250 mL)
  3. washthe organic layer was washed with water and brine
  4. dry with materialIt was then dried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was purified by 100-200 silica column chromatography

출처 및 근거

ORD 기록
ord-a731bf4a9c0d4741b14e384748a5e865
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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