Toluene → 2-chlorobicyclo[2.2.1]hept-5-ene-2-carbonitrile

HRID 749117Notes

Reaction equation

HRID 749117 reaction equation
[Cl:1][C:2](=[CH2:5])[C:3]#[N:4].C1CC=CC=1.[C:11]1([CH3:17])[CH:16]=CC=[CH:13][CH:12]=1>>[Cl:1][C:2]1([C:3]#[N:4])[CH2:16][CH:11]2[CH2:17][CH:5]1[CH:13]=[CH:12]2

Participants

4

Reactant 3

HCID 1140TolueneHCID 7612CyclopentadieneHCID 701982-Chloroacrylonitrile

Product 1

HCID 2432332-chlorobicyclo[2.2.1]hept-5-ene-2-carbonitrileYield 56.5%

Procedure

To a solution of 2-chloroacrylonitrile (50.0 g, 571 mmol) in toluene (150 ml) was slowly added cyclopentadiene (37.7 g, 571 mmol). The reaction was stirred for 60 h at ambient temperature under a nitrogen atmosphere. The reaction was then concentrated by rotary evaporation to remove the majority of the toluene. The compound was purified by vacuum distillation (100-150° C., 15 mm Hg) to afford the nitrile as a white solid (49.7 g, 56.5%).

Workup

  1. concentrationThe reaction was then concentrated by rotary evaporation
  2. customto remove the majority of the toluene
  3. distillationThe compound was purified by vacuum distillation (100-150° C., 15 mm Hg)

Sources & evidence

ORD record
ord-a498c689fb4e483f8b5c0a6798df1b43
Source dataset
uspto-grants-2008_07
Patent number
US07402592B2

Reaction notes

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