Benzene → 2-(4-Bromothiophen-2-yl)-1,3-dioxolane

HRID 2081756Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2081756
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[S:5][CH:6]=1.C1(C)C=CC(S(O)(=O)=[O:16])=CC=1.[CH:20]1[CH:25]=CC=CC=1>>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]2[O:16][CH2:20][CH2:25][O:8]2)[S:5][CH:6]=1

Komponenten

4

Edukt 3

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 877924-Bromothiophene-2-carbaldehyde

Produkt 1

HCID 38572552-(4-Bromothiophen-2-yl)-1,3-dioxolaneAusbeute 72 %

Versuchsvorschrift

In a 100 mL roundbottom flask equipped with a dean stark trap and a reflux condenser, 4-bromothiophene-2-carboxaldehyde (25 g, 131 mMol) and a catalytic amount of p-toluenesulfonic acid were dissolved in benzene (50 mL). The mixture was heated to reflux overnight. The reaction was cooled, washed with sat'd sodium bicarbonate, water, dried (MgSO4) and concentrated. Purification by fractional distillation (80°-90° C., 0.5 mm Hg) afforded 24.23 g (72%) of the desired dioxolane as a clear liquid.

Aufarbeitung

  1. customIn a 100 mL roundbottom flask equipped with a dean stark trap and a reflux condenser
  2. temperatureThe mixture was heated
  3. temperatureto reflux overnight
  4. temperatureThe reaction was cooled
  5. washwashed with sat'd sodium bicarbonate, water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customPurification
  9. distillationby fractional distillation (80°-90° C., 0.5 mm Hg)

Quellen und Nachweise

ORD-Eintrag
ord-410fc2c968474776b0367118b95eccbe
Quelldatensatz
uspto-grants-1993_02
Patentnummer
US05185363

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