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

HRID 237482노트

반응식

HRID 237482 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-e10e31b119794a4995336d41bc01d136
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642585B2

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