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

HRID 1278693Notes

Reaction equation

HRID 1278693 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([CH3:8])[CH:7]=1.C1C(=O)N([Br:17])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([CH:7]=1)[CH2:8][Br:17]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1235275-Bromo-2-fluorotoluene

Product 1

HCID 135532954-Bromo-2-(bromomethyl)-1-fluorobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 5-bromo-2-fluorotoluene (15 g, 0.079 mole) in CCl4 (150 mL) was added NBS (14.2 g, 0.080 mole). The resulting reaction solution was heated under reflux with the starting material being completely consumed within 2 hr. CCl4 was removed under reduced pressure and the residue was diluted dissolved in ether, washed with brine (3×), dried over MgSO4, concentrated. Chromatographed/hexane yielded 5-bromo-2-fluorobenzyl bromide. The product was immediately used for the reaction below.

Workup

  1. customThe resulting reaction solution
  2. temperaturewas heated
  3. temperatureunder reflux with the starting material
  4. custombeing completely consumed within 2 hr
  5. customCCl4 was removed under reduced pressure
  6. additionthe residue was diluted
  7. dissolutiondissolved in ether
  8. washwashed with brine (3×)
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated
  11. customChromatographed/hexane

Sources & evidence

ORD record
ord-72ef93ceac914e4f8336e41ab67bb2f6
Source dataset
uspto-grants-2002_09
Patent number
US06444668B1

Reaction notes

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