Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][C:14]([OH:16])=O.C([Li])CCC.Cl>C1COCC1.CCCCCC>[F:11][C:8]([F:9])([F:10])[C:6]1[CH:7]=[C:2]2[C:3]([CH2:12][CH2:13][C:14]2=[O:16])=[CH:4][CH:5]=1To a solution of 3-[2-bromo-4-(trifluoromethyl)phenyl]propanoic acid (6.40 g, 21.5 mmol) in THF (300 mL) and hexane (80 mL) at −78° C. was added a 2.5 M solution of n-butyllithium in hexane (19 mL). After being stirred for 15 min, the mixture was poured into a 2 N HCl solution (150 mL). The two layers were separated and the water layer was extracted by ether. The combined organic layers were washed with NaHCO3 solution, water, brine, dried over MgSO4 and concentrated. Column chromatography on silica (10-20% EtOAC in hexane) provided the title compound (2.2 g, 51%) as an oil. MS calculated for C10H7F3O: (M+H)+ 201; found 201.0.
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