C[C@H](CN)O[Si](C)(C)C(C)(C)C.Fc1cc(Br)ccc1OCc1ccccc1>CC(=O)O.CC(=O)O.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.Cc1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>C[C@H](CNc1ccc(OCc2ccccc2)c(F)c1)O[Si](C)(C)C(C)(C)CPdOAc2 (0.080 g, 0.36 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.170 g, 0.36 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromo-2-fluorobenzene (1 g, 3.56 mmol), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (0.674 g, 3.56 mmol) and cesium carbonate (1.739 g, 5.34 mmol) in toluene (20 mL) at 120°C under nitrogen. The resulting suspension was stirred at 120 °C for 16 hours. The reaction mixture was diluted with EtOAc (20 mL) and water (20 mL). The biphasic mixture was filtered through celite. The organic layer was separated and washed sequentially with water (50 mL) and saturated brine (50 mL). The organic layer was filtered and dried over Na2SO4, filtered and evaporated to afford crude product. The crude product was evaporated and was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford (R)-4-(benzyloxy)-N-(2-(tert- butyldimethylsilyloxy)propyl)-3-fluoroaniline (0.851 g, 61.4 %) as a orange oil.
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