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

HRID 1444847Notes

Reaction equation

HRID 1444847 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-bbb99f66433e4a998c7bcc4dabe7f010
Source dataset
uspto-grants-2010_02
Patent number
US07662995B2

Reaction notes

Loading…