N-bromobutanimide → 4-(Bromomethyl)-2-chloro-1-fluorobenzene

HRID 582920Notes

Reaction equation

HRID 582920 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:11]=[C:12]([CH3:17])[CH:13]=[CH:14][C:15]=1[F:16]>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Cl:9][C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:17][Br:1]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 27365893-Chloro-4-fluorotoluene

Product 1

HCID 27575424-(Bromomethyl)-2-chloro-1-fluorobenzeneYield 97.9%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

0.05 g of dibenzoyl peroxide and then 6.1 g of N-bromosuccinimide are added to a mixture of 5 g of 3-chloro-4-fluorotoluene and 100 ml of CCl4 and the reaction mixture is refluxed for 12 hours. The insoluble material is filtered off and washed with CCl4. The filtrate is washed with water and with saturated NaCl solution, the organic phase is dried over Na2SO4 and the solvent is evaporated off under vacuum to give 7.5 g of the expected product in the form of an oil, which is used as such.

Workup

  1. temperaturethe reaction mixture is refluxed for 12 hours
  2. filtrationThe insoluble material is filtered off
  3. washwashed with CCl4
  4. washThe filtrate is washed with water and with saturated NaCl solution
  5. dry with materialthe organic phase is dried over Na2SO4
  6. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-27530829b1f64747b7d4ae8f13747156
Source dataset
uspto-grants-1999_07
Patent number
US05925768

Reaction notes

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