C[Si](C)(C)[C:3]([F:6])([F:5])[F:4].Br[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=1[O:18][CH3:19].[F-].[K+].[OH-].[Na+]>CN(C=O)C.CN1C(=O)CCC1.[Cu]I.O>[CH3:19][O:18][C:12]1[C:13]([CH2:17][C:3]([F:6])([F:5])[F:4])=[CH:14][CH:15]=[CH:16][C:11]=1[CH3:10]Trimethyl(trifluoromethyl)silane (25.39 mL, 162.5 mmol) was added to a stirred mixture of 1-bromomethyl-2-methoxy-3-methyl-benzene(19 g, 65 mmol), KF (9.44 g, 162.5 mmol), CuI (37.10 g, 195 mmol) in DMF (75 mL) and NMP (75 mL). The reaction mixture was heated to 55° C. under N2 for 15 hours. The mixture was poured into water, made basic with 1 N NaOH and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated to a black oil. Flash column chromatography (0% to 60% EtOAc in hexanes) gave the product as a yellow oil (12.0 g). LCMS: APCI−VE=203
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