N-bromobutanimide → 2-Bromo-1-(bromomethyl)-4-fluorobenzene

HRID 726153Notes

Reaction equation

HRID 726153 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][Br:10]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 740162-Bromo-4-fluorotoluene

Product 1

HCID 107069772-Bromo-1-(bromomethyl)-4-fluorobenzeneYield 62.4%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-Bromo-4-Fluorotoluene (46.6 g, 0.25 mol, Aldrich), N-bromosuccinimide (46.3 g, 0.26 mol, Aldrich) and benzoyl peroxide (0.5 g, 0.002 mol, Aldrich) in carbon tetrachloride (500 ml) was refluxed and illuminated (250 watt, infrared lamp) for 18 h. After cooling to room temperature, the succinimide was filtered and the filtrate was concentrated in vacuo. Chromatography on silica gel with hexanes as eluent gave 41.8 g (62%) of 2-bromo-1-(bromomethyl)-4-fluorobenzene as a white solid: mp 47°-49° C.

Workup

  1. temperaturewas refluxed
  2. customilluminated (250 watt, infrared lamp) for 18 h
  3. filtrationthe succinimide was filtered
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-68aa5b7044fa4b8fa86210e3c30c27e0
Source dataset
uspto-grants-1998_01
Patent number
US05708033

Reaction notes

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