Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].[Li]CCCC.CCCCCC.[CH:24](=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl>CCOCC.O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([CH:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[OH:31])=[C:3]([C:9]([F:12])([F:11])[F:10])[CH:4]=1To a solution of 1,4-dibromo-2-(trifluoromethyl)benzene (300 mg, 0.987 mmol) in 2 mL of Et2O (C=0.5M) was added dropwise a 1.6M solution of BuLi in hexane (650 μL, 1.05 eq) at −78° C. After 25 min of stirring, benzaldehyde (120 μL, 1.2 eq) was slowly added. The mixture was stirred for 2 h at −78° C. and was allowed to warm to r.t. overnight. Then, the reaction mixture was hydrolyzed with water and with a 1M HCl solution to acidify. The layers were separated. The aqueous layer was extracted with DCM (3×10 mL). The combined organics were washed with brine, dried over MgSO4, filtered and solvents were removed in vacuo. The crude residue was purified by silica gel flash chromatography (cyclohexane/AcOEt 95:5) to afford the desired product in 90% yield (295 mg) as uncoloured oil. 1H NMR (300 MHz, CDCl3) δ 7.80 (d, J=2.1 Hz, 1H), 7.67 (dd, J=8.4, 2.1 Hz, 1H), 7.54 (d, J=8.5 Hz, 1H), 7.39-7.27 (m, 5H), 6.24 (s, 1H), 2.44 (s, OH); 13C NMR (75 MHz, CDCl3) δ 142.3 (C), 141.4 (q, J=1.4 Hz, C), 135.5 (CH), 131.5 (CH), 129.3 (q, J=30.9 Hz, C), 128.8 (q, J=6.1 Hz, CH), 128.7 (CH), 128.0 (CH), 126.5 (CH), 123.5 (q, J=274.6 Hz, C), 121.7 (C), 70.6 (q, J=2.1 Hz, CH); MS (ESI) m/z: 375.0, 377.0 [M−H+HCO2H, 79Br, 81Br]−; 705.2, 707.2 [2M−2H+HCO2H, 79Br, 81Br]−.
Loading…
