Bromine → 1-(4-(Bromomethyl)phenyl)cyclopropanecarbonitrile

HRID 1905412Notes

Reaction equation

HRID 1905412 reaction equation
[C:1]1([CH3:12])[CH:6]=[CH:5][C:4]([C:7]2([C:10]#[N:11])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[Br:13]Br>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:13][CH2:12][C:1]1[CH:2]=[CH:3][C:4]([C:7]2([C:10]#[N:11])[CH2:8][CH2:9]2)=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 986281-(p-Tolyl)cyclopropanecarbonitrile

Product 1

HCID 200354281-(4-(Bromomethyl)phenyl)cyclopropanecarbonitrileYield 93.2%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent2×

Procedure

3.0 Grams (0.02 mole) of 1-p-tolylcyclopropane-1-carbonitrile and 0.1 g (0.0004 mole) of benzoyl peroxide were dissolved in 50 ml of carbon tetrachloride, and 3.2 g of bromine was added dropwise over 30 minutes under reflux. After completion of the addition, reaction was continued for further 30 minutes. After cooling the reaction solution, carbon tetrachloride was removed by evaporation to obtain 4.4 g of 1-(4-bromomethylphenyl)cyclopropane-1-carbonitrile.

Workup

  1. temperatureunder reflux
  2. additionAfter completion of the addition, reaction
  3. customwas removed by evaporation

Sources & evidence

ORD record
ord-c4d3b711cc2546709b28f36bce39e1e0
Source dataset
uspto-grants-1989_06
Patent number
US04843068

Reaction notes

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