Potassium Iodide → 1,1'-Biphenyl, 4'-(bromomethyl)-2-nitro-

HRID 1974592Notes

Reaction equation

HRID 1974592 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.[Br:17]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C.[I-].[K+]>C(Cl)(Cl)(Cl)Cl>[Br:17][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

6

Reactant 4

HCID 4875Potassium IodideHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 104431944'-Methyl-2-nitro-1,1'-biphenyl

Product 1

HCID 117790721,1'-Biphenyl, 4'-(bromomethyl)-2-nitro-Yield 102.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 4-methyl-2'-nitro-1,1'-biphenyl (Step J) (6.0 g, 28.2 mmol), N-bromosuccinimide (4.99 g, 28.2 mmol) and AIBN (653 mg) in 75 mL of carbon tetrachloride was heated at reflux until a negative potassium iodide test was obtained (1.5 h). The reaction mixture was cooled and filtered. The filtrate was evaporated under vacuum to yield 8.41 g of crude product. 1H NMR revealed the product composition was approximatly 75% monobromo and 10% dibromo, in addition to 15% of unreacted starting material. 1H NMR (200 MHz,CDCl3): 4.53 (s, 2H), 7.2-7.7 (m, 7H), 7.85 (m, 1H). EI-MS: calculated for C14H10BrN 272; found 272,274 (M+).

Workup

  1. customwas obtained (1.5 h)
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customThe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-00a5fe09cb6148e29523fdf8392d8357
Source dataset
uspto-grants-1994_02
Patent number
US05283241

Reaction notes

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