1-Indanone (≥99%, ReagentPlus, Sigma-Aldrich)

Phenylmagnesium Bromide (2.8 M solution in 2-MeTHF, Acros Organics)

2-MeTHF (≥99%, Anhydrous, Sigma-Aldrich)

Iodine (≥99.8%, ACS Reagent, Sigma-Aldrich)

Diethyl Ether (Sigma-Aldrich)

Saturated Ammonium Chloride

10% Aqueous Sodium Thiosulfate

The synthesis was performed using standard Schlenk techniques under a nitrogen atmosphere. To a sealed roundbottom flask charged with 1-indanone (2.00 g, 0.0151 mol), anhydrous 2-MeTHF (76 mL) was added. Phenylmagnesium Bromide (5.4 mL, 0.0151 mol, 2.8 M solution in 2-MeTHF) was added dropwise to the reaction mixture at 0 ^oC. The reaction mixture was allowed to return to room temperature. The reaction mixture was then stirred at 40 ^oC for 20 h. The reaction mixture was quenched and washed with saturated ammonium chloride (3 x 15 mL) and extracted with diethyl ether (3 x 15 mL). The organic layer was dried over magnesium sulfate, filtered into a roundbottom flask, and further eluted with diethyl ether (10 mL). The solvent was evaporated under reduced pressure. Crude 1-phenyl-indanol was isolated. To the roundbottom flask charged with the crude mixture was added: iodine (383 mg, 1.51 mmol). The neat reaction mixture was stirred at RT for 20 h. TLC was used to monitor the reaction.* The reaction was quenched with aqueous sodium thiosulfate (10% aqueous, 3 x 15 mL) and diethyl ether (3 x 15 mL). The reaction mixture was dried over magnesium sulfate, filtered into a roundbottom flask, and further eluted with diethyl ether (10 mL). The solvent was evaporated under reduced pressure, yielding a tan oil. The product was then purified using flash chromatography (95:5 Hex:EtOAc) to yield a yellow oil, 3-phenyl-indene (1.88 g, 65%).    

*An aliquot was removed from the crude reaction mixture and diluted for TLC.

The yield of the 2 g synthesis was determined by isolating the product. This synthesis was attempted at a 3 g scale and the isolated yield was determined to be 53%. This synthesis was also attempted at a 100 mg scale and the isolated yield was determined to be 65%.

A saturated solution of sodium chloride (Brine) was used to remove emulsions during the washing phases.

¹H NMR (CDCl₃, 500 MHz): δ ppm 3.56 (d, J = 2.3 Hz, 2H), 6.64 (t, J = 2.0 Hz, 1H), 7.27-7.68 (m, 9H)

¹H NMR is similar to previously printed spectra. See lead reference.

Stavber, G.; Zupan, M.; Stavber, S. Tetrahedron Lett., 2006, 47, 8463-8466. http://dx.doi.org/10.1016/j.tetlet.2006.09.154