Benzoyl Peroxide → 1-Bromo-4-(bromomethyl)-2-fluorobenzene

HRID 2172648Notes

Reaction equation

HRID 2172648 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[F:9].[Br:10]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:10])=[CH:4][C:3]=1[F:9]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimide2×HCID 5732804-Bromo-3-fluorotoluene

Product 1

HCID 116661761-Bromo-4-(bromomethyl)-2-fluorobenzeneYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-bromo-3-fluorotoluene (21.5 g, 0.114 moles) in acetonitrile (200 ml) is added with N-bromosuccinimide, (NBS; 21.2 g, 0.119 moles). The mixture is refluxed, added with dibenzoyl peroxide (1.4 g, 0.004 moles), refluxed for 3 hour, then cooled at room temperature, and extracted with water. The aqueous phase is discarded, and the organic phase is washed with brine, dried over sodium sulphate, and concentrated under vacuum to give an oil (27.1 g, 90% yield).

Workup

  1. temperatureThe mixture is refluxed
  2. temperaturerefluxed for 3 hour
  3. extractionextracted with water
  4. washthe organic phase is washed with brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d8c00fdaf249490b847f66ff29fd70ca
Source dataset
uspto-grants-2015_06
Patent number
US09056818B2

Reaction notes

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