Thionyl Chloride → 1-(Benzo[b]thiophen-3-yl)-3-chloropropan-2-one

HRID 1671634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1671634
[Cl:1][CH2:2]C(=O)CC1SC=CC=1.[S:11]1[CH:15]=[C:14]([CH2:16][C:17]([OH:19])=O)[C:13]2[CH:20]=[CH:21][CH:22]=[CH:23][C:12]1=2.S(Cl)(Cl)=O>>[S:11]1[CH:15]=[C:14]([CH2:16][C:17](=[O:19])[CH2:2][Cl:1])[C:13]2[CH:20]=[CH:21][CH:22]=[CH:23][C:12]1=2

Komponenten

4

Edukt 3

HCID 24386Thionyl ChlorideHCID 70799Benzo[b]thiophene-3-acetic acidHCID 161002061-Chloro-3-(thiophen-2-yl)propan-2-one

Produkt 1

HCID 161001791-(Benzo[b]thiophen-3-yl)-3-chloropropan-2-oneAusbeute 56 %

Versuchsvorschrift

The procedure described above for the synthesis of 1-chloro-3-(thiophen-2-yl)propan-2-one was followed. To prepare the acid chloride, 2-(benzo[b]thiophen-3-yl)acetic acid (1.00 g, 5.20 mmol) was added to 6 mL thionyl chloride in a 25 mL round-bottomed flask. The mixture was stirred overnight at room temperature, and the thionyl chloride then removed in vacuo and the residue azeotroped twice with toluene. The acid chloride was then reacted with diazomethane and HCl. The crude product was purified by flash chromatography over silica gel (2-30% ethyl acetate in hexanes) to give pure material (0.661 g, 56% yield): 1H NMR (400 MHz, CDCl3) δ 4.12 (s, 2H) 4.14 (d, J=1.0 Hz, 2H) 7.36-7.44 (m, 3H) 7.67-7.71 (m, 1H) 7.87-7.90 (m, 1H).

Aufarbeitung

  1. customthe thionyl chloride then removed in vacuo
  2. customthe residue azeotroped twice with toluene
  3. customThe acid chloride was then reacted with diazomethane and HCl
  4. customThe crude product was purified by flash chromatography over silica gel (2-30% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-84bc3fb38d564d5f8f6e969faae83354
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994333B2

Notizen zur Reaktion

Wird geladen…