Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:3]=1.C([Mg]Cl)(C)C.[Li]CCCC.CN([CH:26]=[O:27])C>C1COCC1>[C:9]([C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([F:8])[CH:5]=1)[CH:26]=[O:27])([CH3:12])([CH3:11])[CH3:10]Bromo-3-tert-butyl-5-fluorobenzene (323.2 g, 1.4 moles) was dissolved in THF (3.3 L) and cooled −10° C. iPrMgCl (2M solution in THF, 0.5 eq, 350 mL) was added over 20 min, followed by nBuLi (2.5M solution in hexanes, 1.0 eq, 560 mL) over two hours. DMF (4 eq, 450 mL) was added over one hour then stirred for 45 minutes and quenched with 3M HCl (1000 mL). The layers were separated and the aqueous fraction was diluted with water (1 L) and extracted with ethyl acetate (1 L). The organic fractions were combined and washed with water (2×2 L). The organic fraction was concentrated to provide an orange oil (252 g, quant), used directly in the next reaction.
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