Azobisisobutyronitrile → 4'-(Bromomethyl)-2-chloro-1,1'-biphenyl

HRID 890739Notes

Reaction equation

HRID 890739 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[Cl:14])=[CH:4][CH:3]=1.C1C(=O)N([Br:22])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Br:22][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[Cl:14])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 123227902-Chloro-4'-methyl-1,1'-biphenyl

Product 1

HCID 222468324'-(Bromomethyl)-2-chloro-1,1'-biphenylYield 61.3%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4′-methyl-2-chloro-biphenyl (1.08 g, 5.33 mmol), NBS (1.14 g, 6.40 mmol) and AIBN (175 mg, 1.06 mmol) in CCl4 (37 mL) was heated at reflux for 3 h. The reaction mixture was diluted with CH2Cl2 and the organic solution was washed sequentially with aqueous saturated NaHCO3 (2×), water (1×), and brine (1×). The organic solution was dried over MgSO4, filtered, and concentrated in vacuo. The product was purified by flash chromatography (hexanes to 5% EtOAc/hexanes) to afford the title compound (920 mg). 1H NMR (CDCl3 400 MHz) δ 7.63–7.25 (m, 8H), 4.56 (s, 2H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. washthe organic solution was washed sequentially with aqueous saturated NaHCO3 (2×), water (1×), and brine (1×)
  4. dry with materialThe organic solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by flash chromatography (hexanes to 5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-87650318e2d6487aa8d4478e041bd512
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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