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

HRID 237482ノート

反応式

HRID 237482 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-e10e31b119794a4995336d41bc01d136
出典データセット
uspto-grants-2014_02
特許番号
US08642585B2

反応ノート

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