Acetonitrile → 6-Bromo-benzo[b]thiophene-2-carboxylic acid methyl ester

HRID 523555

Reaktionsgleichung

Reaktionsgleichung von HRID 523555
[CH3:1][O:2][C:3](=[O:6])[CH2:4][SH:5].C(#N)C.[Br:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[C:13](F)[CH:12]=1.C(OCC)(=O)C>CCCCCC>[CH3:1][O:2][C:3]([C:4]1[S:5][C:13]2[CH:12]=[C:11]([Br:10])[CH:18]=[CH:17][C:14]=2[CH:15]=1)=[O:6]

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 16907Methyl ThioglycolateHCID 1435174-Bromo-2-fluorobenzaldehyde

Produkt 1

HCID 224740786-Bromo-benzo[b]thiophene-2-carboxylic acid methyl esterAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

TEA (1.29 g, 12.85 mmol) and mercapto-acetic acid methyl ester (1.14 g, 10.83 mmol) were added to acetonitrile (50 mL) previously purged with argon (10 minute). This was followed by the addition of 4-bromo-2-fluoro-benzaldehyde (2 g, 9.852 mmol) and the resulting mixture was heated to reflux at 85° C. overnight. The reaction was monitored by TLC (20% ethyl acetate in hexane). The reaction mixture was cooled, concentrated, basified with 10% NaOH solution and extracted with ethyl acetate to afford the crude product. Purification by column chromatography on silica gel (5% ethyl acetate in hexane) afforded 2.4 g of the product (90% yield).

Aufarbeitung

  1. custompreviously purged with argon (10 minute)
  2. temperaturethe resulting mixture was heated
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated
  5. extractionextracted with ethyl acetate
  6. customto afford the crude product
  7. customPurification by column chromatography on silica gel (5% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-bc9a41da7205448d9ab8ff0daecd3eeb
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09339501B2

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