[K].Br[CH:3]([CH:7]([CH3:9])[CH3:8])[C:4]([OH:6])=[O:5].[Br:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[C:13]([F:18])[CH:12]=1.[OH-].[Na+]>CCOCC.C(Cl)(Cl)Cl>[Br:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15][C@H:3]([C:4]([OH:6])=[O:5])[CH:7]([CH3:9])[CH3:8])=[C:13]([F:18])[CH:12]=1To the potassium salt of α-bromoisovaleric acid (1.42 g) is added 4-bromo-2-fluoroaniline (1.9 g). The mixture is heated at 125° under nitrogen for 3.5 hr and then cooled to RT. The reaction product is poured into 2 M NaOH and ether/chloroform. The basic phase is separated and acidified with conc. HCl and then extracted into ether, washed with saturated NaCl solution, dried over calcium sulfate and evaporated to yield N-(4-bromo-2-fluorophenyl)valine.
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