Azobisisobutyronitrile → 4-(2-Methoxyphenyl)benzyl bromide

HRID 458512Notes

Reaction equation

HRID 458512 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1.C1C(=O)N([Br:23])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>ClC(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[CH:11][C:12]([CH2:15][Br:23])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 103135412-Methoxy-4'-methyl-1,1'-biphenyl

Product 1

HCID 219041364-(2-Methoxyphenyl)benzyl bromide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-methoxy-4′-methylbiphenyl, 160 mg (0.81 mmol), NBS, 158 mg (0.91 mmol), and AIBN, 1 mg (0.006 mmol) were suspended in 7 mL tetrachloromethane, and refluxed for 24 hours. The product was filtered, and the solvent removed from the filtrate by rotary evaporation. Equal amounts of diethyl ether and water were added and the product extracted. The ether layer was separated and dried over MgSO4, filtered, and the solvent removed. 4-(2-Methoxyphenyl)benzyl bromide, 128 mg, was obtained as an oil.

Workup

  1. temperaturerefluxed for 24 hours
  2. filtrationThe product was filtered
  3. customthe solvent removed from the filtrate by rotary evaporation
  4. additionEqual amounts of diethyl ether and water were added
  5. extractionthe product extracted
  6. customThe ether layer was separated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe solvent removed

Sources & evidence

ORD record
ord-d5ec89be604148009bd67110a711d7e4
Source dataset
uspto-grants-2007_03
Patent number
US07192918B2

Reaction notes

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