[CH3:1][C:2]1([CH3:8])[C:6](=[O:7])[CH:5]=[CH:4][CH2:3]1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[C:12]([F:19])[CH:11]=1.C([O-])(=O)C.[Na+].[Sb](Cl)(Cl)Cl>CC([O-])=O.CC([O-])=O.[Pd+2].C(O)(=O)C>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH:4]2[CH2:5][C:6](=[O:7])[C:2]([CH3:8])([CH3:1])[CH2:3]2)=[C:12]([F:19])[CH:11]=1A solution of 5,5-dimethylcyclopent-2-en-1-one (42.0 g, 343.15 mmol), 4-chloro-2-fluorophenylboronic acid (94.47 g, 514.72 mmol), sodium acetate (56.30 g, 686.30 mmol), acetic acid (1130 mL), Pd(OAc)2 (7.70 g, 34.31 mmol), and antimony trichloride (7.83 g, 34.31 mmol) are stirred at ambient temperature for 16 hours. The solvent is evaporated to low volume and the residual acetic acid is removed using toluene. MTBE (500 mL) is added and the resulting precipitate is filtered off and discarded. The MTBE solution is washed with water (500 mL), aq. NaHCO3 (2×300 mL), dried over MgSO4, filtered, and concentrated to dryness. The residue is purified by silica gel flash chromatography, eluting with hexane to hexane 10% MTBE to give the title compound (72 g, 87%). 1H NMR (300.16 MHz, CDCl3) δ 7.21-7.06 (m, 3H), 3.67-3.59 (m, 1H), 2.81-2.72 (m, 1H), 2.41-2.31 (m, 1H), 2.21 (ddd, J=12.6, 6.3, 2.2 Hz, 1H), 1.89 (t, J=12.3 Hz, 1H), 1.159 (s, 3H), 1.137 (s, 3H).
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