Hydrochloric Acid → 5-Bromo-3-(2-chloro-ethyl)-thiophene-2-carbonyl chloride

HRID 69505Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 69505
[Br:1][C:2]1[S:11][C:5]2[C:6](=O)O[CH2:8][CH2:9][C:4]=2[CH:3]=1.[OH-:12].[Li+].[ClH:14].S(Cl)([Cl:17])=O>C1COCC1.O.CO.C1(C)C=CC=CC=1>[Br:1][C:2]1[S:11][C:5]([C:6]([Cl:14])=[O:12])=[C:4]([CH2:9][CH2:8][Cl:17])[CH:3]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 24386Thionyl ChlorideHCID 689922162-Bromo-4,5-dihydro-thieno[2,3-c]pyran-7-one

Produkt 1

HCID 866351075-Bromo-3-(2-chloro-ethyl)-thiophene-2-carbonyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

A mixture of 2-Bromo-4,5-dihydro-thieno[2,3-c]pyran-7-one (400 mg), Lithium hydroxide (246.7 mg) in THF/water/methanol (1.7 mL/1.7 mL/0.2 mL) was stirred for 6 h at room temperature. Then the reaction mixture was acidified with 2 N HCl and the aqueous phase was extracted with ethyl acetate, dried over sodium sulfate and the solvent removed. The obtained crude product was heated to reflux with thionylchloride (6.2 mL) for 2 h. Toluene was added and the volatile components removed in vacuum. This step was repeated twice.

Aufarbeitung

  1. extractionthe aqueous phase was extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customthe solvent removed
  4. customThe obtained crude product
  5. temperaturewas heated
  6. customthe volatile components removed in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1417653a73c04630b7daef51b2b559c0
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822495B2

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