Ethylene Glycol → 2-(5-Bromo-2-fluorophenyl)-1,3-dioxolane

HRID 1271914Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1271914
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].O.CC1C=CC(S(O)(=O)=O)=CC=1.[CH2:23](O)[CH2:24][OH:25].C1(C)C=CC=CC=1>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:7]2[O:25][CH2:24][CH2:23][O:8]2)[CH:9]=1

Komponenten

6

Edukt 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 7363275-Bromo-2-fluorobenzaldehyde

Produkt 1

HCID 184555852-(5-Bromo-2-fluorophenyl)-1,3-dioxolane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5-Bromo-2-fluorobenzaldehyde (14.6 mL, 0.123 mol, Avocado) is combined with 4-methylbenzenesulfonic acid hydrate (2.34 g, 12.0 mmol, Aldrich), ethylene glycol (13.7 mL, 0.25 mol, Mallinkrodt) and toluene (75 mL). The mixture is heated to reflux overnight. The resulting solution is diluted into EtOAc (100 mL) and washed 2× with saturated NaHCO3, 1× with water and 1× with brine (170 mL ea). The organic layer is dried over Na2SO4 and filtered. The solvent is removed by rotary evaporation and the product is purified on a Biotage Flash 75L (800 g silica) cartridge using 96:3:1 heptane:EtOAc:TEA as eluent.

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureto reflux overnight
  3. washwashed 2× with saturated NaHCO3, 1× with water and 1× with brine (170 mL ea)
  4. dry with materialThe organic layer is dried over Na2SO4
  5. filtrationfiltered
  6. customThe solvent is removed by rotary evaporation
  7. customthe product is purified on a Biotage Flash 75L (800 g silica) cartridge

Quellen und Nachweise

ORD-Eintrag
ord-6d00bbb6730c42659ee94c1be1203e50
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07208490B2

Notizen zur Reaktion

Wird geladen…