Phenolate Sodium → Silafluofen

HRID 2073923

Reaktionsgleichung

Reaktionsgleichung von HRID 2073923
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([Si:10]([CH3:23])([CH3:22])[CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16](Cl)[CH:15]=2)=[CH:6][CH:5]=1)[CH3:2].[C:24]1([O-:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[Na+]>[Cu]Cl.COCCOCCOCCOCCOC>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([Si:10]([CH3:23])([CH3:22])[CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([O:30][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:15]=2)=[CH:6][CH:5]=1)[CH3:2]

Komponenten

5

Edukt 2

HCID 4445035Phenolate SodiumHCID 109481121-((3-(3-Chloro-4-fluorophenyl)propyl)dimethylsilanyl)-4-ethoxybenzene

Produkt 1

HCID 92430SilafluofenAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 62652Cuprous chlorideKatalysatorHCID 8925TetraglymeLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 456.2 g (1.30 mol) of (4-ethoxyphenyl)-(dimethyl)-(3-(3-chloro-4-fluorophenyl)propyl)silane, 232.2 g (2.00 mol) of sodium phenolate, 13 g of copper(I) chloride and 500 ml of tetraglyme was heated to 240°-255° C. for 1.5 h. After cooling the reaction mixture to 90° C., a larger part of the solvent was removed by distillation at 90°-140° C. internal temperature and 0.4 Torr (about 400 g). The crude product was then stirred at room temperature with 500 ml of 2N sodium hydroxide solution and extracted twice using 800 ml of hexane each time. The organic extracts were washed five times with 300 ml of water each time, dried over sodium sulfate and evaporated. The crude product thus obtained (486.1 g/92%) was distilled over a 50 cm split tube column. 233 g (44%) of (4-ethoxyphenyl)-(dimethyl)-(3-(4-fluoro-3-phenoxyphenyl)propyl)silane were obtained as a colorless oil of b.p.0.04 =208°-212° C., the purity of which was determined to be 95.2% by gas chromatography.

Aufarbeitung

  1. temperaturewas heated to 240°-255° C. for 1.5 h
  2. customa larger part of the solvent was removed by distillation at 90°-140° C. internal temperature and 0.4 Torr (about 400 g)
  3. extractionextracted twice
  4. washThe organic extracts were washed five times with 300 ml of water each time
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe crude product thus obtained (486.1 g/92%)
  8. distillationwas distilled over a 50 cm
  9. customsplit tube column

Quellen und Nachweise

ORD-Eintrag
ord-6c80d61f41ee4aac817d0c93a785c085
Quelldatensatz
uspto-grants-1990_04
Patentnummer
US04920212

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