Benzene, 2-bromo-1,4-dimethyl- → (2,5-Dimethylphenyl)(dimethyl)octylsilane

HRID 747079

反応式

HRID 747079 の反応式
[Mg].Br[C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[CH3:10].[CH3:11][Si:12](Cl)([CH3:21])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[Cl-].[NH4+]>O1CCCC1>[CH3:11][Si:12]([CH3:21])([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[CH3:10]

参加物

6

反応物 4

HCID 11121Benzene, 2-bromo-1,4-dimethyl-HCID 25517Ammonium ChlorideHCID 87482ChlorodimethyloctylsilaneHCID 5462224Magnesium

生成物 1

HCID 58738483(2,5-Dimethylphenyl)(dimethyl)octylsilane収率 42.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
70 °C

実験手順

1.95 g (80.2 mmol) of finely cut magnesium metal was placed in a 200 ml four-necked flask, and 50 ml of anhydrous tetrahydrofuran was further charged. The mixture was heated up to 70° C. while stirring, and 50 ml of a solution of 5 g (27.0 mmol) of 2-bromo p-xylene in anhydrous tetrahydrofuran was added dropwise while caring for steep reaction (reflux). After completion of the addition, it was refluxed for 30 minutes, then, cooled to 40° C., and to this was added 6.7 g (32.4 mmol) of dimethyloctylsilyl chloride while stirring. The solution was again heated and refluxed for 3 hours. The reaction mixture was charged in an aqueous saturated ammonium chloride solution, and extracted (toluene/water) and the organic phase was dried over sodium sulfate. After concentration, the product was purified and isolated by silica gel column chromatography (n-hexane) to obtain 3.19 g of 2-(dimethyloctylsilyl)-p-xylene.

後処理

  1. customwhile caring for steep reaction (reflux)
  2. additionAfter completion of the addition, it
  3. temperaturewas refluxed for 30 minutes
  4. temperaturecooled to 40° C.
  5. stirringwhile stirring
  6. temperatureThe solution was again heated
  7. temperaturerefluxed for 3 hours
  8. extractionextracted (toluene/water)
  9. dry with materialthe organic phase was dried over sodium sulfate
  10. concentrationAfter concentration
  11. customthe product was purified
  12. customisolated by silica gel column chromatography (n-hexane)

出典と根拠

ORDレコード
ord-81637682aa414a1891c98ee78018a83c
出典データセット
uspto-grants-2008_07
特許番号
US07396571B2

関連ノート

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