p-Bromochlorobenzene → (Chloromethyl)(4-chlorophenyl)dimethylsilane

HRID 2413292Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2413292
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1.Cl[Si:10]([CH2:13][Cl:14])([CH3:12])[CH3:11].C([Li])CCC>O1CCCC1.CCCCCC.CCOCC.[Cl-].[Li+]>[Cl:14][CH2:13][Si:10]([C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1)([CH3:12])[CH3:11]

Komponenten

8

Edukt 3

HCID 7806p-BromochlorobenzeneHCID 74393Silane, chloro(chloromethyl)dimethyl-HCID 178418339Butyllithium

Produkt 1

HCID 2733089(Chloromethyl)(4-chlorophenyl)dimethylsilaneAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittelHCID 433294Lithium ChlorideLösungsmittel

Versuchsvorschrift

A solution of 9.6 g (0.050 mol) of 4-bromochlorobenzene and 6.6 ml (7.2 g, 0.050 mol) of chloro(chloromethyl)dimethylsilane in 75 ml of tetrahydrofuran was stirred at -78° under nitrogen while 31 ml (0.050 mol) of 1.6 molar n-butyllithium in hexane was added dropwise. The resulting clear solution was allowed to warm to room temperature, diluted with ether until no more lithium chloride precipitated, and filtered. Evaporation of the filtrate left 10.6 g of a light yellow liquid, which was distilled to give 6.0 g (55%) of the title compound as a colorless liquid: bp 54°-58° C. (0.05 mm); ir (neat) 2910, 1560, 1470, 1370, 1250, 1080, 1010, 840, 805, 790, 740 cm-1 ; nmr (CDCl3) 0.4 (6H, s), 2.9 (2H, s), 7.1-7.6 (4H, q).

Aufarbeitung

  1. additionwas added dropwise
  2. customprecipitated
  3. filtrationfiltered
  4. customEvaporation of the filtrate
  5. waitleft 10.6 g of a light yellow liquid, which
  6. distillationwas distilled

Quellen und Nachweise

ORD-Eintrag
ord-58178a78257048aa8400632e9ceb7255
Quelldatensatz
uspto-grants-1985_01
Patentnummer
US04496551

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