Dimethyl Sulfoxide → 2-Bromo-5-chlorothiophene-3-carbaldehyde

HRID 870030Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 870030
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Br:11][C:12]1[S:13][C:14]([Cl:19])=[CH:15][C:16]=1[CH2:17][OH:18].C(N(CC)CC)C>ClCCl>[Br:11][C:12]1[S:13][C:14]([Cl:19])=[CH:15][C:16]=1[CH:17]=[O:18]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 57900970(2-Bromo-5-chlorothiophen-3-yl)methanol

Produkt 1

HCID 509991562-Bromo-5-chlorothiophene-3-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of DMSO (2.10 mL, 29.7 mmol) in dichloromethane (50 mL) at −78° C. was added oxalyl chloride (1.90 mL, 26.8 mmol) dropwise and the mixture was stirred for 30 min. at the temperature. To it was then added (2-bromo-5-chloro-3-thienyl)methanol from Example 1, Step 2 (4.50 g, 19.8 mmol, crude) in dichloromethane (25 mL) via a cannula and the resultant solution was stirred for 30 min. Triethylamine (6.40 mL, 45.5 mmol) was added in one portion and the mixture was stirred at −78° C. for 30 min. and allowed to warm slowly in air. The mixture was concentrated in vacuo and then resuspended in ether and then filtered. The filtrate was concentrated in vacuo to give the desired product. The crude was used directly without further purification.

Aufarbeitung

  1. stirringthe mixture was stirred at −78° C. for 30 min.
  2. temperatureto warm slowly in air
  3. concentrationThe mixture was concentrated in vacuo
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b7e78f9b57464da1a2d4f9cbfb5c49a6
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969394B2

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