Azobisisobutyronitrile → tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylate

HRID 1851877Notes

Reaction equation

HRID 1851877 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.C1C(=O)N([Br:28])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:28][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 9838270tert-Butyl 4'-methyl[1,1'-biphenyl]-2-carboxylate

Product 1

HCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
100 °C

Procedure

To a 500 mL round-bottom flask was added tert-butyl 4′-methylbiphenyl-2-carboxylate (7.04 g, 26.23 mmol), NBS (5.14 g, 28.85 mmol), AIBN (0.43 g, 2.62 mmol) and CCl4 (200 mL). The reaction mixture was refluxed for 2 h at 100° C. The completion of the reaction was monitored by analytical HPLC. The reaction mixture was allowed to cool to room temperature and filtered. The filtrate was concentrated to obtain the crude product which was purified by flash chromatography (AcOEt/Hexane 0→30%) to obtain the title compound.

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customto obtain the crude product which
  5. customwas purified by flash chromatography (AcOEt/Hexane 0→30%)

Sources & evidence

ORD record
ord-d162cbf3f5e64d40853e3f45791afc61
Source dataset
uspto-grants-2015_02
Patent number
US08957093B2

Reaction notes

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