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

HRID 1872502Notes

Reaction equation

HRID 1872502 reaction equation
[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

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 80597m-Bromobenzenethiol

Product 1

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

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d813842bd05144a6b9854ea40e25d04a
Source dataset
uspto-grants-2000_08
Patent number
US06110910

Reaction notes

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