Reaktion #1680798

Reaktionsgleichung

HCl

ethyl 4-[(4-fluorophenyl)thio]-3-oxocyclohexanecarboxylate

AlCl3

→

title compound

Ausbeute 78.1%

Ethyl 8-fluoro-1,2,3,4-tetrahydrodibenzo[b,d]thiophene-2-carboxylate

Ausbeute 78.1%

Lösungsmittel

water

dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   ExtraktionThe aqueous mixture was extracted with EtOAc
3. 3
   WaschenThe organic layer was washed with water
4. 4
   Trocknenbrine, then was dried over MgSO4
5. 5
   Einengenconcentrated to an oil
6. 6
   SonstigePurification by chromatography on silica gel

Vorschrift

To a room temperature solution of ethyl 4-[(4-fluorophenyl)thio]-3-oxocyclohexanecarboxylate (3.4 g, 11.5 mmol) in dichloroethane (100 mL) was added AlCl3 (3.7 g, 27.6 mmol). The mixture was heated to 80° C. for 1 hour. After cooling to room temperature, the reaction was diluted with water and acidified with 1 N HCl. The aqueous mixture was extracted with EtOAc. The organic layer was washed with water then brine, then was dried over MgSO4 and concentrated to an oil. Purification by chromatography on silica gel afforded 2.5 g (77%) of the title compound as semi-solid: MS (+) 278 (M)+.

Quelle