Chlorotrimethylsilane → (4-Bromo-3,5-dimethylphenyl)trimethylsilane

HRID 237482Notes

Reaction equation

HRID 237482 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5](Br)=[CH:4][C:3]=1[CH3:10].C([Li])CCC.Cl[Si:17]([CH3:20])([CH3:19])[CH3:18]>C(OCC)C.O1CCCC1.CCCCCC>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([Si:17]([CH3:20])([CH3:19])[CH3:18])=[CH:4][C:3]=1[CH3:10]

Participants

7

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 27580472,5-Dibromo-1,3-dimethylbenzeneHCID 178418339Butyllithium

Product 1

HCID 86697146(4-Bromo-3,5-dimethylphenyl)trimethylsilane

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 2,5-dibromo-1,3-dimethylbenzene (500 mg) in diethylether (3 mL) and tetrahydrofuran (2.5 mL) is cooled to −78° C. and treated dropwise with n-butyllithium (200 μL of a 10 M solution in n-hexane). The mixture is stirred for 1 hour and treated dropwise with chloro-trimethyl-silane (275 μL). After stirring for 2 hours the reaction is quenched by addition of saturated aqueous NH4Cl solution. The mixture is extracted with diethylether. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→90:10) to give the title compound. Yield: 260 mg; Mass spectrum (ESI+): m/z=279 [M+Na]+.

Workup

  1. stirringAfter stirring for 2 hours the reaction
  2. customis quenched by addition of saturated aqueous NH4Cl solution
  3. extractionThe mixture is extracted with diethylether
  4. dry with materialThe organic phase is dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→90:10)

Sources & evidence

ORD record
ord-e10e31b119794a4995336d41bc01d136
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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