Hexane → 5-Bromo-3-methyl-1-benzothiophene

HRID 572396Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 572396
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10](=O)[CH3:11])=[CH:4][CH:3]=1.CCCCCC>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[S:8][CH:9]=[C:10]([CH3:11])[C:4]=2[CH:3]=1

Komponenten

4

Edukt 2

HCID 8058HexaneHCID 8219021-((4-Bromophenyl)thio)propan-2-one

Produkt 1

HCID 141757645-Bromo-3-methyl-1-benzothiopheneAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Polyphosphoric acid (7 g) was added to a solution of 1-(4-bromo-phenylsulfanyl)-propan-2-one (I-24a: 2.0 g, 8.163 mmol) in toluene (10 mL) and the resulting mixture was heated to 100° C. for 5 hours. The reaction was monitored by TLC (100% hexane). The reaction mixture was cooled to room temperature, quenched with ice, basified with potassium carbonate (pH˜8) and extracted with ethyl acetate. The organic layer was concentrated to yield the crude product. Purification by column chromatography on silica gel (100% hexane) afforded 1.2 g of product (66% yield)

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with ice
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic layer was concentrated
  5. customto yield the crude product
  6. customPurification by column chromatography on silica gel (100% hexane)

Quellen und Nachweise

ORD-Eintrag
ord-1cf08af0785f4d9784603395beac3d68
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029399B2

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