Sodium Hydroxide → 2-Bromo-5-phenylthiophene-3-carboxylic acid

HRID 590991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 590991
[Br:1][C:2]1[S:3][C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][C:6]=1[C:7]([O:9]C)=[O:8].[OH-].[Na+]>C(O)C.O>[Br:1][C:2]1[S:3][C:4]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:5][C:6]=1[C:7]([OH:9])=[O:8]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 70818321Methyl 2-bromo-5-phenylthiophene-3-carboxylate

Produkt 1

HCID 581103102-Bromo-5-phenylthiophene-3-carboxylic acidAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of methyl 2-bromo-5-phenylthiophene-3-carboxylate (11c) (290 mg, 0.97 mmol) and sodium hydroxide (156 mg, 3.90 mmol) in a mixture of ethanol (6 mL) and water (2 mL) was refluxed for 30 minutes. The mixture was concentrated in vacuo. The remained aqueous layer was washed with diethyl ether (5 mL), acidified with 1N hydrochloric acid until pH 3 and was extracted with dichloromethane (2×10 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to provide the desired acid (11d) (260 mg, 0.92 mmol, 95%), which was used without further purification.

Aufarbeitung

  1. temperaturewas refluxed for 30 minutes
  2. concentrationThe mixture was concentrated in vacuo
  3. washThe remained aqueous layer was washed with diethyl ether (5 mL)
  4. extractionwas extracted with dichloromethane (2×10 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-735c9d9aa1e643a28b3df0ee1d37425a
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238026B2

Notizen zur Reaktion

Wird geladen…