N-bromobutanimide → 1-Bromo-3-(bromomethyl)-2,4-difluorobenzene

HRID 1794132Notes

Reaction equation

HRID 1794132 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([CH3:9])[C:3]=1[F:10].[Br:11]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([CH2:9][Br:11])[C:3]=1[F:10]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 112872263-Bromo-2,6-difluorotoluene

Product 1

HCID 222200841-Bromo-3-(bromomethyl)-2,4-difluorobenzeneYield 105.3%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Bromo-2,4-difluoro-3-methyl-benzene (22 g, 0.106 M) and N-bromosuccinimide (22.7 g, 0.128 M) were dissolved in tetrachloromethane (800 mL). Dibenzoylperoxide (0.52 g, 2 mM) was added and the mixture was irradiated for 1 h. Succinimide was removed by filtration of the cooled mixture and the filtrate was washed with water. The water phase was extracted with dichloromethane. Organic phases were pooled, dried with MgSO4 and and evaporated to yield a yellowish oil (32 g). The residue was purified by column chromatography (silica gel; n-hexane) to yield 28.4 g (94%) of the title compound as a colorless oil. MS (EI): 286.0 (M)+.

Workup

  1. customthe mixture was irradiated for 1 h
  2. customSuccinimide was removed by filtration of the cooled mixture
  3. washthe filtrate was washed with water
  4. extractionThe water phase was extracted with dichloromethane
  5. dry with materialdried with MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-843d8c12655c4b1d841861447f58e22a
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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