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

HRID 2269199Notes

Reaction equation

HRID 2269199 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[Br:21].[Cl:22]C(Cl)(Cl)C(C(Cl)(Cl)Cl)=O>O1CCCC1>[Cl:22][C:19]1[C:14]([F:13])=[C:15]([Br:21])[CH:16]=[CH:17][C:18]=1[F:20]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 8303HexachloroacetoneHCID 676741-Bromo-2,4-difluorobenzeneHCID 178418339Butyllithium

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 19 ml (0.135 mole) of diisopropylamine in 125 ml of tetrahydrofuran (THF) 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 to 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 to room temperature
  3. customAfter evaporation of the solvent
  4. distillationthe residue is distilled under vacuum

Sources & evidence

ORD record
ord-9940c86259974f108bd1b595aad9432b
Source dataset
uspto-grants-2001_12
Patent number
US06329391B1

Reaction notes

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