Benzoyl Peroxide → 4-(Bromomethyl)-3-chlorobenzonitrile

HRID 923231Notes

Reaction equation

HRID 923231 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[C:5]#[N:6].C1C(=O)N([Br:18])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 888943-Chloro-p-toluonitrile

Product 1

HCID 130420934-(Bromomethyl)-3-chlorobenzonitrile

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3-Chloro-4-methylbenzonitrile (2.34 g, 15.4 mmol), NBS (3.0 g, 16.9 mmol) and benzoyl peroxide (0.37 g, 1.54 mmol) are taken up in carbon tetrachloride (50 mL, 0.3M) and refluxed until the reaction is judged complete by TLC. The mixture is then allowed to cool to room temperature and is filtered. The filtrate is concentrated and purified via flash column chromatography (0-5% EtOAc/hexanes) to give 4-bromomethyl-3-chlorobenzonitrile as a white solid. HRMS (ESI) m/z 229.9133 (229.9193 calcd for C8H6ClBrN, M+H).

Workup

  1. temperaturerefluxed until the reaction
  2. filtrationis filtered
  3. concentrationThe filtrate is concentrated
  4. custompurified via flash column chromatography (0-5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2ddec42240054073969210c8d5924af3
Source dataset
uspto-grants-2016_03
Patent number
US09278969B2

Reaction notes

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