Ethylene Glycol → 2-(4-Bromo-2-Fluorophenyl)-1,3-Dioxolane

HRID 78227

Reaktionsgleichung

Reaktionsgleichung von HRID 78227
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:10])[CH:3]=1.[CH2:11](O)[CH2:12][OH:13].C(=O)([O-])O.[Na+]>C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[O:13][CH2:12][CH2:11][O:7]2)=[C:4]([F:10])[CH:3]=1

Komponenten

6

Edukt 3

HCID 174Ethylene GlycolHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 516892Sodium Bicarbonate

Produkt 1

HCID 219386012-(4-Bromo-2-Fluorophenyl)-1,3-DioxolaneAusbeute 102,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-KatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 4-bromo-2-fluorobenzaldehyde (10 g, 49.3 mmol), ethylene glycol (27.5 mL, 493 mmol), camphorsulfonic acid (115 mg, 0.493 mmol), and toluene (250 mL) was stirred for 5 hours under reflux. The mixture was cooled to room temperature and a saturated sodium hydrogencarbonate aqueous solution was added thereto. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (12.5 g). The title compound was used in the following reaction without any further purification.

Aufarbeitung

  1. temperatureunder reflux
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-af5d92c52a2140d79ab52bb625bdc812
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841327B2

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