N-bromobutanimide → 1,1'-Biphenyl, 4'-(bromomethyl)-2-nitro-

HRID 326759

Reaction equation

HRID 326759 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])=[CH:4][CH:3]=1.C1C(=O)N([Br:24])C(=O)C1>N(C(C)(C)C#N)=NC(C)(C)C#N.C(Cl)(Cl)(Cl)Cl>[Br:24][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 104431944'-Methyl-2-nitro-1,1'-biphenyl

Product 1

HCID 117790721,1'-Biphenyl, 4'-(bromomethyl)-2-nitro-Yield 101.2%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture containing 6.5 g of 4-methyl-2'-nitrobiphenyl, 5.42 g of NBS, 118 mg of azo-bis-isobutyronitrile and 500 ml of carbon tetrachloride is refluxed for 5 hours. It is cooled to 0° C. and filtered and the filtrate is concentrated to give 9 g of an oily product, which is used as such in the next step.

Workup

  1. temperatureis refluxed for 5 hours
  2. filtrationfiltered
  3. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-24278e22323e4ebf969f711e19fec804
Source dataset
uspto-grants-1993_12
Patent number
US05270317

Linked notes

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