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 1N 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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