N-bromobutanimide → 4-(Bromomethyl)naphthalene-1-carbonitrile

HRID 1951397Notes

Reaction equation

HRID 1951397 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]#[N:13])=[CH:4][CH:3]=1.[Br:14]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl>[Br:14][CH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]#[N:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1420471-Cyano-4-methylnaphthalene

Product 1

HCID 124330084-(Bromomethyl)naphthalene-1-carbonitrileYield 74.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2.50 g (14.95 mmol) of 4-methyl-1-naphthonitrile are dissolved in 40 ml of tetrachloromethane and 3.19 g (17.94 mmol) of N-bromosuccinimide and 245 mg (1.50 mmol) of 2,2′-azobis-2-methyl-propanenitrile are added. The mixture is stirred at the reflux temperature overnight. After cooling, the product is filtered off. 2.75 g (74.7% of theory) of 4-(bromomethyl)-1-naphthonitrile are obtained in a purity of 90% and are reacted without further purification.

Workup

  1. temperatureAfter cooling
  2. filtrationthe product is filtered off

Sources & evidence

ORD record
ord-34c1388349e54a8591ee74115032d73f
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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