[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:9][C:10]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:11]=1[CH:12]=[O:13]>CCOCC.C1COCC1.CCOC(C)=O>[Br:9][C:10]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:11]=1[CH:12]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[OH:13]A solution of PhMgBr (1M in THF, 2.60 mL, 2.60 mmol) was added dropwise to a −78° C. solution of 2-bromo-5-fluorobenzaldehyde (0.4742 g, 2.336 mmol) in Et2O (5 mL) and THF (1.3 mL), stirred for 15 minutes, allowed to warm to room temperature, stirred for 30 minutes, diluted with EtOAc, washed with water and saturated NH4Cl, dried (Na2SO4), and filtered. The residue was chromatographed on SiO2 (0-10% Et2O/hexanes) to give 561.0 mg of the title compound as a clear gum. 1H NMR (300 MHz, DMSO-d6) δ 7.60 (dd, 1H), 7.46 (dd, 1H), 7.21-7.36 (m, 5H), 7.10 (ddd, 1H), 6.21 (s, 1H), 5.88 (s, 1H).
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