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In a 3-neck round-bottomed flask equipped with a reflux condenser and a nitrogen inlet, TiCl4 (0.51 mL, 4.67 mmol) was slowly added to a suspension of zinc powder (0.63 g, 9.60 mmol) in dry THF (13 mL) at room temperature. The reaction mixture was heated at reflux for 2.5 h. The reaction mixture was taken out of the oil bath and a solution of (4-bromophenyl)(4-hydroxyphenyl)methanone (2) (0.35 g, 1.26 mmol) and bicyclo[3.3.1]nonan-9-one (0.52 g, 3.79 mmol) in dry THF (13 mL) was added. The reaction mixture was heated at reflux for 2 h. The reaction mixture was allowed to cool at RT. Water (10 mL) was added to the reaction mixture via a syringe followed by 10% K2CO3 (10 mL). The reaction mixture was filtered through a pad of Celite. The pad of Celite washed with EtOAc. The filtrate was transferred to a separatory funnel and the layers were separated. The organic layer washed with brine, dried (MgSO4), filtered, and the filtrate was concentrated to give an oily residue. The crude product was adsorbed onto silica and purified by flash column chromatography using SiO2 and a hexanes:EtOAc gradient (100:0 to 75:25) to afford compound 43 as a white powder (0.32 g, 67%). 1H NMR (400 MHz, DMSO-d6): δ 1.50-1.54 (m, 2H), 1.71-1.73 (m, 8H), 1.93-1.99 (m, 2H), 2.60 (s, 1H), 6.67 (d, J=8.4 Hz, 2H), 6.87 (d, J=8.5 Hz, 2H), 7.02 (d, J=8.5 Hz, 2H), 7.46 (d, J=8.3 Hz, 2H), 9.32 (s, 1H).

1. customIn a 3-neck round-bottomed flask equipped with a reflux condenser and a nitrogen inlet
2. temperatureThe reaction mixture was heated
3. temperatureat reflux for 2.5 h
4. temperatureThe reaction mixture was heated
5. temperatureat reflux for 2 h
6. filtrationThe reaction mixture was filtered through a pad of Celite
7. washThe pad of Celite washed with EtOAc
8. customThe filtrate was transferred to a separatory funnel
9. customthe layers were separated
10. washThe organic layer washed with brine
11. dry with materialdried (MgSO4)
12. filtrationfiltered
13. concentrationthe filtrate was concentrated
14. customto give an oily residue
15. custompurified by flash column chromatography