Azobisisobutyronitrile → 1-Bromo-4-(bromomethyl)-2-fluorobenzene

HRID 1881405Notes

Reaction equation

HRID 1881405 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[F:9].C1C(=O)N([Br:17])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:17])=[CH:4][C:3]=1[F:9]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 5732804-Bromo-3-fluorotoluene

Product 1

HCID 116661761-Bromo-4-(bromomethyl)-2-fluorobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-bromo-3-fluorotoluene (39.4 g, 0.21 mol), NBS (38.1 g, 0.22 mol) and AIBN (5 g, 0.03 mol) in 250 mL CH2Cl2 was heated at reflux for 6 h. After cooling to room temperature, the reaction mixture was filtered, and the filtrate was washed with water, brine, and concentrated under vacuum to afford 1-bromo-4-(bromomethyl)-2-fluorobenzene, which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 h
  3. filtrationthe reaction mixture was filtered
  4. washthe filtrate was washed with water, brine
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f675da05961e4f23a556e5de8d10a3e4
Source dataset
uspto-grants-2012_11
Patent number
US08318767B2

Reaction notes

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