Reaktion #57019

Reaktionsgleichung

AlCl3

3-(2-bromo-phenyl)-propionic acid

oxalyl chloride

→

4-Bromoindan-1-one

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenAs the mixture was concentrated
2. 2
   workup.DISSOLUTIONthe residue was dissolved in CH2Cl2
3. 3
   SonstigeAfter 1 h the mixture was quenched with water
4. 4
   Sonstigethe layers were separated
5. 5
   ExtraktionThe aqueous layer was extracted with Et2O (3×150 mL)
6. 6
   Waschenthe combined organic extracts were washed with H2O (3×100 mL), saturated NaHCO3 (3×100 mL), brine (1×100 mL)
7. 7
   Trocknendried over MgSO4
8. 8
   Einengenconcentrated

Vorschrift

4-Bromo-indan-1-one was obtained by the following procedure: A solution of 3-(2-bromo-phenyl)-propionic acid (commercially available from Oakwood Products) (15.0 g, 65.5 mmol) in CH2Cl2 at 0° C. was reacted with oxalyl chloride (7.2 mL, 1.5 eq) followed by 2-3 drops of DMF. The mixture was stirred until no more gas evolution was observed. As the mixture was concentrated and the residue was dissolved in CH2Cl2, cooled to 0° C., and treated with AlCl3 (9.6 g, 1.1 eq). After 1 h the mixture was quenched with water and the layers were separated. The aqueous layer was extracted with Et2O (3×150 mL) and the combined organic extracts were washed with H2O (3×100 mL), saturated NaHCO3 (3×100 mL), brine (1×100 mL), dried over MgSO4 and concentrated. 4-Bromoindan-1-one, 10.5 g (76%) was obtained by chromatography using 10% EtOAc:hexane as eluant. Use of 4-bromo-indan-1-one in Method NINETEEN produced 4-(4-bromo-indan-2-yl)-1,3-dihydro-imidazole-2-thione (Compound 149).

Quelle