反応 #9377

反応方程式

AlCl3

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

oxalyl chloride

→

4-Bromoindan-1-one

溶媒

CH2Cl2

反応条件

後処理

1. 1
   濃縮As the mixture was concentrated
2. 2
   workup.DISSOLUTIONthe residue was dissolved in CH2Cl2
3. 3
   その他After 1 h the mixture was quenched with water
4. 4
   その他the layers were separated
5. 5
   抽出The aqueous layer was extracted with Et2O (3×150 mL)
6. 6
   洗浄the combined organic extracts were washed with H2O (3×100 mL), saturated NaHCO3 (3×100 mL), brine (1×100 mL)
7. 7
   乾燥dried over MgSO4
8. 8
   濃縮concentrated

実験手順

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).

出典