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

HRID 1879431Notes

Reaction equation

HRID 1879431 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(Cl)(Cl)(Cl)Cl>[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-fluorobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 4-bromo-3-fluorotoluene (10 g, 0.053 moles) in carbon tetrachloride (100 ml) is added with N-bromosuccinimide, (NBS; 14 g, 0.08 moles). The mixture is refluxed, added with dibenzoyl peroxide (100 mg, 0.4 mmoles), refluxed for 1 hour, then cooled at room temperature and extracted with water. The aqueous phase is discarded, the organic phase is washed with brine, dried over sodium sulfate and concentrated under vacuum to give an oil (16 g) which is subjected to chromatography on a silica gel column (150 g), eluting with hexane, to afford the product.

Workup

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

Sources & evidence

ORD record
ord-fceaa1e5341a4b5c8f8d63c0d2e3f1cc
Source dataset
uspto-grants-2012_11
Patent number
US08314268B2

Reaction notes

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