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

HRID 22268

反応式

HRID 22268 の反応式
[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

参加物

4

反応物 2

HCID 7855AcrylonitrileHCID 80597m-Bromobenzenethiol

生成物 1

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

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e11ad11d2499429e80643360e0a1b5f0
出典データセット
uspto-grants-1995_06
特許番号
US05428040

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