Thionyl Chloride → 2-Chloromethylbenzofuran

HRID 1030267

Reaktionsgleichung

Reaktionsgleichung von HRID 1030267
S(Cl)([Cl:3])=O.[O:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH:7]=[C:6]1[CH2:14]O>N1C=CC=CC=1.C(Cl)Cl.O>[Cl:3][CH2:14][C:6]1[O:5][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH:7]=1

Komponenten

6

Edukt 2

HCID 24386Thionyl ChlorideHCID 27762631-Benzofuran-2-Ylmethanol

Produkt 1

HCID 1843482-ChloromethylbenzofuranAusbeute 70,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1049PyridineKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Thionyl chloride (5.14 mL, 70.46 mmol) was added dropwise to a solution of benzofuran-2-methanol (3.58 g, 23.48 mmol) and pyridine (10 drops) in methylene chloride (60 mL). Stirring was continued at room temperature for 18 hours. The mixture was carefully diluted with water and extracted with methylene chloride. The organic extracts were washed with aqueous sodium bicarbonate, dried (MgSO4) and concentrated to afford crude product which was purified by flash column chromatography (10% EtOAc/hexanes) to afford 2.77 g (69%) of pure product as a yellow oil.

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. washThe organic extracts were washed with aqueous sodium bicarbonate
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto afford crude product which
  6. customwas purified by flash column chromatography (10% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c012e877cce043cf851bd73ad11690a6
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05104892

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