C([Li])CCC.C([Mg]Cl)CCC.Br[C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([Br:23])[CH:14]=1.CN([CH:27]=[O:28])C.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[Br:23][C:15]1[CH:14]=[C:13]([CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=1)[CH:27]=[O:28]To a stirred solution of n-butyl lithium (2.5 M in hexanes, 0.8 eq.) in toluene (0.2 M) at −15° C. was added dropwise n-butyl magnesium chloride (2.0 M in THF, 0.4 eq.). After 20 min, a solution of 1,3-dibromo-5-(trifluoromethyl)benzene (1 eq.) in toluene was added over 10 min. The reaction mixture thus obtained was stirred at −15° C. for 2 h before DMF (3 eq.) was added. The reaction was allowed to warm to 0° C. After 45 min, saturated aqueous ammonium chloride was added. The reaction mixture was extracted with ethyl acetate. The combined organic extracts were then washed with brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc) afforded the title compound.
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