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

HRID 857333Notes

Reaction equation

HRID 857333 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH3:9].C1C(=O)N([Br:17])C(=O)C1>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:17]

Participants

5

Reactant 2

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

Product 1

HCID 107069772-Bromo-1-(bromomethyl)-4-fluorobenzeneYield 98.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2-bromo-4-fluorotoluene (50 g, 265 mmol) in CCl4 (1 L) was added NBS (52 g, 291 mmol) and 300 mg of benzoyl peroxide. The mixture was heated to reflux and stirred for 30 minutes under a sun lamp. The reaction mixture was cooled and filtered on a SiO2 pad eluted with hexanes. The filtrate was concentrated to give 70 g of the title compound as a colorless oil and used as such.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered on a SiO2 pad
  5. washeluted with hexanes
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-66efbf0ed0ca4cc0b53220eeb4961c41
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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