Dichloromethane → HCID 178423640, compound

Participants

Reaction Steps

N-Butyllithium (1.6M in hexanes, 4.2 mL, 6.7 mmol) was added dropwise to a solution of 2-(4-methyl)phenyl)indene (1.323 g, 6.4 mmol) in Et2O (20 mL). The red-orange solution was stirred at ambient temperature for 30 min after which time the solvent was removed in vacuo. In a drybox, to the resulting solid was added ZrCl4 (0.754 g, 3.2 mmol). The solids were cooled to -78° C. and methylene chloride (60 mL) was slowly added. The solution was warmed to room temperature and kept there overnight. The resulting yellow-orange turbid solution was then filtered over a plug of Celite and the Celite was washed with CH2Cl2 until the washings were colorless (ca. 60 mL). The product was recrystallized from CH2Cl2 /hexane at -18° C. Yield: 577 mg (31%). 1H NMR (C6D6, 23° C., 400 MHz): d 7.36 (d, J=8 Hz, 4H); 7.11 (m, 4H); 7.02 (d, J=8 Hz, 4H); 6.92 (m, 4H); 6.43 (s, 4H, Cp-H); 2.17 (s, 6H, CH3). C, H analysis (crystallizes with 1/2 CH2Cl2): Anal. Found (Calcd.): C, 63.21 (63.46); H, 4.41 (4.42).

Provenance & Evidence