Chloroform → 1-(2,2-Dichloro-1-fluoro-cyclopropyl)-4-methyl-benzene

HRID 2244325Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2244325
[OH-].[Na+].[F:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)=[CH2:5].[CH:13]([Cl:16])(Cl)[Cl:14]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:14][C:13]1([Cl:16])[CH2:5][C:4]1([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)[F:3]

Komponenten

5

Edukt 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 150837261-(1-Fluoroethenyl)-4-methylbenzene

Produkt 1

HCID 687008961-(2,2-Dichloro-1-fluoro-cyclopropyl)-4-methyl-benzeneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 66133Benzyl triethylammonium chlorideKatalysator

Versuchsvorschrift

50% aq. sodium hydroxide solution (4.4 mL, 54 mmol) was added dropwise at 0° C. to a solution of 1-(1-fluoro-vinyl)-4-methyl-benzene (J. Med. Chem. 2004, 47, 5860; 1.84 g, 13.5 mmol) and benzyltriethylammonium chloride (123 mg, 0.54 mmol) in chloroform (20 mL), then after 30 min the ice bath was removed and stirring continued over 16 h. Ice water was added, the organic layer was subsequently washed with 0.1 M aq. hydrochloric acid solution, 5% aq. sodium hydrogencarbonate solution and brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane) afforded the title compound (2.54 g, 86%). Light yellow liquid, MS (EI) 218.0 (M+).

Aufarbeitung

  1. customafter 30 min the ice bath was removed
  2. additionIce water was added
  3. washthe organic layer was subsequently washed with 0.1 M aq. hydrochloric acid solution, 5% aq. sodium hydrogencarbonate solution and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-44784dd5b7b644aba88d65efac85eeac
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678818B2

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