Benzoyl Peroxide → 1-(Bromomethyl)-2-fluoro-4-iodobenzene

HRID 341038

Reaction equation

HRID 341038 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[Br:10]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:10][CH2:9][C:3]1[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 1234922-Fluoro-4-iodotoluene

Product 1

HCID 222404061-(Bromomethyl)-2-fluoro-4-iodobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-Fluoro-4-iodo-1-methylbenzene (2.0 g, 8.6 mmol) was dissovled in carbon tetrachloride (10 mL), treated with N-bromosuccinimide (1.5 g, 8.6 mmol, 1 equiv) and benzoyl peroxide (9.0 mg, 0.004 equiv) and placed into an oil bath preheated to 80° C. for 3 hours. The mixture was cooled to ambient temperature, filtered and the filtrate was concentrated in vacuo, providing the titled compound.

Workup

  1. customplaced into an oil bath
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6317748c3b054fe5b1ecf65ca3bcedde
Source dataset
uspto-grants-2014_11
Patent number
US08895580B2

Linked notes

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