4-Bromobenzophenone → HCID 68505673, compound

Participants

Reaction Steps

To a stirred suspension of Zn powder (4.80 g, 73.5 mmol) and THF (100 mL) under N2 was added TiCl4 (3.9 mL, 35.7 mmol), dropwise. The resulting yellow suspension was stirred at RT for 45 min followed by reflux for 2.5 h. A solution of cycloheptanone (3.42 g, 30.6 mmol) and 4-bromobenzophenone (2.54 g, 9.75 mmol) in THF (40 mL) was added dropwise to the refluxing reaction over 15 min. After 2 h the reaction was cooled to RT and then quenched by sequential dropwise addition of water (75 mL) and 10% aqueous Na2CO3 (75 mL). The mixture was stirred overnight at RT then diluted with EtOAc (300 mL) and filtered through a celite pad. The celite pad was rinsed with EtOAc (250 mL) and the colorless filtrates transferred to a separatory funnel. The organic fraction was washed with brine (300 mL), dried (Na2SO4) and concentrated to 6.50 g of a colorless oil. The oil was purified by column chromatographed on silica gel (150 g) with hexanes followed by 2% EtOAc:hexanes and the product 1 isolated as a colorless oil that solidified on standing (2.54 g, 76%). 1H NMR (300 MHz, DMSO-d6): δ 1.59 (s, 8H), 2.27 (br s, 4H), 7.15-7.39 (m, 7H), 7.55 (d, J=8.3 Hz, 2H).

Provenance & Evidence