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Chlorotrimethylsilane → (4-Chloro-2,6-difluorophenyl)trimethylsilane

HRID 1772867
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1772867
[Li]CCCC.[Cl:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]([F:14])[CH:8]=1.Cl[Si:16]([CH3:19])([CH3:18])[CH3:17]>C1COCC1>[Cl:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([Si:16]([CH3:19])([CH3:18])[CH3:17])=[C:9]([F:14])[CH:8]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6397ChlorotrimethylsilaneHCID 137000Benzene, 1-chloro-3,5-difluoro-HCID 178418339Butyllithium

Produkt 1

HCID 18935733(4-Chloro-2,6-difluorophenyl)trimethylsilane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

A solution of 2.5M n-BuLi in hexanes (60 ml, 0.15 mol) was added dropwise to a solution of 1-chloro-3,5-difluorobenzene (19.2 g, 0.13 mol) in THF (200 mL) cooled to −70° C. under Ar. After the addition was complete, the mixture was stirred for 1 h before a solution of chlorotrimethylsilane (21.7 g, 0.2 mol) in THF (25 mL) was added dropwise. The reaction was allowed to warm to rt with stirring overnight before cooling and quenching with H2O. The phases were separated and pentane (200 mL) was added; after washing with H2O the solution was dried over MgSO4 and carefully concentrated in vacuo to yield the title compound as a solution in THF (46 g) which was in the next step without further purification.

Aufarbeitung

  1. additionAfter the addition
  2. additionwas added dropwise
  3. temperatureto warm to rt
  4. temperaturebefore cooling
  5. customquenching with H2O
  6. customThe phases were separated
  7. additionpentane (200 mL) was added
  8. washafter washing with H2O the solution
  9. dry with materialwas dried over MgSO4
  10. concentrationcarefully concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6d3fd43fc00d4eeca191889ae9abdcfd
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09249160B2

Notizen zur Reaktion

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