Dichloromethane → 2-(1-Phenyl-cyclohexyl)-thiophene

HRID 1170562Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1170562
[C:1]1([C:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:13]1[CH:17]=[CH:16][CH:15]=[CH:14]1.ClCCl>Br.C(O)(=O)C>[C:1]1([C:7]2([C:14]3[S:13][CH:17]=[CH:16][CH:15]=3)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 3

HCID 6344DichloromethaneHCID 8030ThiopheneHCID 130431-Phenylcyclohexene

Produkt 1

HCID 669681192-(1-Phenyl-cyclohexyl)-thiophene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 260Hydrogen BromideLösungsmittel

Versuchsvorschrift

Phenyl cyclohexene (50 mg) and thiophene (100 mg) were dissolved in 33% HBr in acetic acid (0.5 mL). The mixture was stirred at room temperature over night. Tlc indicated full conversion of the starting material. Dichloromethane (10 mL) was added. The organic phase was washed with saturated NaHCO3 (3×10 mL), dried Na2SO4 and concentrated in vacuo. The desired product was afforded after flash chromatography (eluent: dichloromethane). Yield: 39 mg. LC/MS purity (UV/MS): 100/90%, Rt 6.22 min. M+1: 243

Aufarbeitung

  1. washThe organic phase was washed with saturated NaHCO3 (3×10 mL), dried Na2SO4
  2. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-72242455545b499ba3bfa33ff5185577
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07825265B2

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