Acrylonitrile → 3-[(3-Bromophenyl)thio]propionitrile

HRID 22268

반응식

HRID 22268 반응식
[Br:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.[C:9](#[N:12])[CH:10]=[CH2:11]>[OH-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]([S:8][CH2:11][CH2:10][C:9]#[N:12])[CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 7855AcrylonitrileHCID 80597m-Bromobenzenethiol

생성물 1

HCID 186867423-[(3-Bromophenyl)thio]propionitrile수율 93.7%

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

실험 절차

3-Bromothiophenol (10 g, 52.9 mmmol) was dissolved in acrylonitrile (11.28 g, 213 mmol). Triton B (1 mL) was added, at which time the reaction mixture became exothermic and began to reflux without added heat. The mixture was allowed to cool to room temperature, poured into cold aqueous sodium hydroxide (2%; 200 mL), and extracted with diethyl ether. The organic layer was dried, filtered and evaporated to provide 12 g (93%) of 3-[(3-bromophenyl)thio]propionitrile as a tan oil; 1H NMR (CDCl3) δ7.54 (s, 1H), 7.42 (d, 1H), 7.32 (d, 1H), 7.25-7.15 (m, 2H), 3.15 (t, 2H), 2.62 (t, 2H); Mass spectrum m/z 261, 259 (M+NH4).

후처리

  1. additionTriton B (1 mL) was added, at which time the reaction mixture
  2. temperatureto reflux
  3. additionwithout added
  4. temperatureheat
  5. extractionextracted with diethyl ether
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. customevaporated

출처 및 근거

ORD 기록
ord-e11ad11d2499429e80643360e0a1b5f0
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428040

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