Chlorotrimethylsilane → 1,2-Difluoro-3-trimethylsilylbenzene

HRID 257685

Reaction equation

HRID 257685 reaction equation
C([Li])CCC.[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13].[CH3:14][Si:15]([CH3:18])([CH3:17])Cl.C1COCC1>CCCCCC.O>[F:6][C:7]1[C:8]([F:13])=[CH:9][CH:10]=[CH:11][C:12]=1[Si:15]([CH3:18])([CH3:17])[CH3:14]

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8028TetrahydrofuranHCID 97061,2-DifluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 108993711,2-Difluoro-3-trimethylsilylbenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

12.5 ml of a 1.6-molar solution of n-butyllithium in hexane is added dropwise at 0° C. to a mixture of 0.02 mol of 1,2-difluorobenzene, 0.02 mol of trimethylchlorosilane and 25 ml of THF. After stirring at room temperature for 1.5 hours, the reaction mixture is poured into water, the phases are separated, and the aqueous phase is extracted with 2×50 ml of methylene chloride. Drying over magnesium sulfate, evaporation of the solvent and chromatography give the pure product.

Workup

  1. customthe phases are separated
  2. extractionthe aqueous phase is extracted with 2×50 ml of methylene chloride
  3. dry with materialDrying over magnesium sulfate, evaporation of the solvent and chromatography
  4. customgive the pure product

Sources & evidence

ORD record
ord-8afda83419114c30a43bb1c65f1f85f2
Source dataset
uspto-grants-1993_11
Patent number
US05262556

Linked notes

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