Chlorotrimethylsilane → (2-Chloro-6-fluoro-3-methoxyphenyl)trimethylsilane

HRID 1172824

Reaktionsgleichung

Reaktionsgleichung von HRID 1172824
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[Li]C(C)(C)C.CCCCC.[CH3:21][Si:22]([CH3:25])([CH3:24])Cl.C(=O)(O)[O-].[Na+]>C1COCC1>[F:8][C:6]1[CH:5]=[CH:4][C:3]([O:9][CH3:10])=[C:2]([Cl:1])[C:7]=1[Si:22]([CH3:25])([CH3:24])[CH3:21]

Komponenten

7

Edukt 5

HCID 6397ChlorotrimethylsilaneHCID 8003PentaneHCID 516892Sodium BicarbonateHCID 27735802-Chloro-4-fluoroanisoleHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 46941339(2-Chloro-6-fluoro-3-methoxyphenyl)trimethylsilane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-4-fluoroanisole (16.5 g, 100 mmol) in THF (500 mL) cooled at −75° C. was added dropwise a solution of t-BuLi in pentane (1.7 M, 61.8 mL, 105 mmol). The reaction was kept at −75° C. for 15 min, quenched at −75° C. with trimethylchlorosilane (19.0 mL, 150 mmol) and finally poured into a saturated solution of sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated. The residue was purified by chromatography on silica gel eluting with 20:1 hexane:diethyl ether to give the title product.

Aufarbeitung

  1. washThe organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on silica gel eluting with 20:1 hexane

Quellen und Nachweise

ORD-Eintrag
ord-cbd6a7b66c6640aebfde53b5897cfb8c
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834036B2

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