Diisopropylamine → 1-Bromo-3-chloro-2,4-difluorobenzene

HRID 1699997

Reaction equation

HRID 1699997 reaction equation
C(NC(C)C)(C)C.[F:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[Br:16].[Cl:17]C(Cl)(Cl)C(C(Cl)(Cl)Cl)=O>C([Li])CCC>[Cl:17][C:14]1[C:9]([F:8])=[C:10]([Br:16])[CH:11]=[CH:12][C:13]=1[F:15]

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 8303HexachloroacetoneHCID 676741-Bromo-2,4-difluorobenzene

Product 1

HCID 27732561-Bromo-3-chloro-2,4-difluorobenzene

Reagents, catalysts & solvents 1

HCID 178418339ButyllithiumSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 19 ml (0.135 mole) of diisopropylarnine in 125 ml of tetrahydroflran (TBF) cooled at −20° C. is added 80 ml of n-butyllithium (1.6 M in hexane). The temperature is raised to 0° C. for 5 minutes and lowered to −78° C. Then 25 g (0.129 mole) of 2,4-difluoro-bromobenzene is then added and the reaction is stirred at −65° C. for 2 hours. Then, 25 ml (0.164 mole) of hexachloroacetone is added and the solution is warmed at room temperature. After evaporation of the solvent, the residue is distilled under vacuum to give the desired product.

Workup

  1. customlowered to −78° C
  2. temperaturethe solution is warmed at room temperature
  3. customAfter evaporation of the solvent
  4. distillationthe residue is distilled under vacuum

Sources & evidence

ORD record
ord-8c047c2ef56049ac90d663ea63b103bc
Source dataset
uspto-grants-2002_02
Patent number
US06348624B1

Linked notes

Loading…