N-bromobutanimide → 3-(Bromomethyl)-4-methoxybenzonitrile

HRID 745251Notes

Reaction equation

HRID 745251 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[CH3:11].C1C(=O)N([Br:19])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:11][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:3]=1[O:2][CH3:1])[C:7]#[N:8]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 136216134-Methoxy-3-methylbenzonitrile

Product 1

HCID 136553283-(Bromomethyl)-4-methoxybenzonitrileYield 70.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To 9.8 g of 4-methoxy-3-methylbenzonitrile, were added 150 ml of carbon tetrachloride, 10 g of NBS, and 0.4 g of BPO. The mixture was heated under reflux for 2.5 hours. The reaction mixture was cooled in ice, filtered from insolubles and concentrated under reduced pressure. The residue was admixed with n-hexane, stirred for 30 minutes, and collected by filtration to yield 9 g of 3-bromomethyl-4-methoxybenzonitrile; m.p. 102°-103° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2.5 hours
  3. temperatureThe reaction mixture was cooled in ice
  4. filtrationfiltered from insolubles
  5. concentrationconcentrated under reduced pressure
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-bf0ec713c34940b3bb1285c9aeecc1d4
Source dataset
uspto-grants-1986_07
Patent number
US04598077

Reaction notes

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