2-Methylbenzo(b)thiophene → 2-(2-Methyl-benzo[b]thiophen-3-ylsulfanyl)-benzoic acid methyl ester

HRID 493097

Reaktionsgleichung

Reaktionsgleichung von HRID 493097
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]Cl)=[O:4].[CH3:13][C:14]1[S:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[CH:15]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11][C:15]1[C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[S:18][C:14]=1[CH3:13]

Komponenten

5

Edukt 3

HCID 709522-Methylbenzo(b)thiopheneHCID 6451240Aluminum(III) ChlorideHCID 122235372-(Methoxycarbonyl)phenyl sulfenyl chloride

Produkt 1

HCID 688980832-(2-Methyl-benzo[b]thiophen-3-ylsulfanyl)-benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-(Methoxycarbonyl)phenyl sulfenyl chloride (10 mL 0.29 M solution in 1,2-dichloro-ethane, 2.9 mmol) is added to a solution of 2-methyl-benzo[b]thiophene (445 mg, 3mmol) in 5 mL 1,2-dichloro-ethane. The reaction mixture is cooled to 0° C. Aluminium chloride (400 mg, 3 mmol) is added and the reaction mixture is stirred for 4 hours at room temperature. The reaction is quenched with water. The organic phase is washed with brine, dried with MgSO4 and concentrated in vacuo. The residue is purified by flash chromatography on silica gel using ethyl acetate-heptane as eluent. This furnishes 651 mg (69%) of the title compound as an oil.

Aufarbeitung

  1. customThe reaction is quenched with water
  2. washThe organic phase is washed with brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-7f52d5d71db94ef4b42538e74fd4c716
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07534791B2

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