Chloroform → 3-Chloro-5-methyl-2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiophene

HRID 2353370Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2353370
[CH3:1][C:2]1[CH:26]=[CH:25][C:5]2[S:6][C:7]([C:9]3[CH:14]=[CH:13][C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[C:11]([C:21]([F:24])([F:23])[F:22])[CH:10]=3)=[CH:8][C:4]=2[CH:3]=1.C(Cl)(Cl)[Cl:28]>>[Cl:28][C:8]1[C:4]2[CH:3]=[C:2]([CH3:1])[CH:26]=[CH:25][C:5]=2[S:6][C:7]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[C:11]([C:21]([F:22])([F:23])[F:24])[CH:10]=1

Komponenten

3

Edukt 2

HCID 6212ChloroformHCID 684528005-Methyl-2-[2-(trifluoromethyl)[1,1'-biphenyl]-4-yl]-1-benzothiophene

Produkt 1

HCID 684539433-Chloro-5-methyl-2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiopheneAusbeute 56 %

Versuchsvorschrift

To a solution of 5-methyl-2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiophene (184 mg, 0.5 mmol) in CHCl3 (2.5 mL) is added SO2Cl2 (44 μL, 1.1 eq.). The mixture is heated to reflux overnight (about 14 hours). All the solvent is removed under reduced pressure. The residue is extracted with CH2Cl2 (50 mL), washed with saturated aqueous NaHCO3, brine, dried over MgSO4, filtered, and concentrated to give an oil. The mixture is purified by column chromatography (EtOAc/Hexane, gradient) to give 112 mg of 3-chloro-5-methyl-2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiophene in 56% yield.

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureto reflux overnight (about 14 hours)
  3. customAll the solvent is removed under reduced pressure
  4. extractionThe residue is extracted with CH2Cl2 (50 mL)
  5. washwashed with saturated aqueous NaHCO3, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give an oil
  10. customThe mixture is purified by column chromatography (EtOAc/Hexane, gradient)

Quellen und Nachweise

ORD-Eintrag
ord-e06a7a7745a54c318301fa6f4cf24d0a
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07750021B2

Notizen zur Reaktion

Wird geladen…