C1(P(C2CCCCC2)[C:8]2C=CC=[CH:10][C:9]=2[C:14]2C=CC=CC=2N(C)C)CCCCC1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:39]([O-:42])(=[O:41])[CH3:40].Br[C:44]1[CH:49]=[CH:48][C:47]([F:50])=[CH:46][C:45]=1[CH3:51]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[F:50][C:47]1[CH:48]=[CH:49][C:44]([CH2:40][C:39]([O:42][C:9]([CH3:14])([CH3:10])[CH3:8])=[O:41])=[C:45]([CH3:51])[CH:46]=1To a 2 L flask containing 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl.(3.76 g) and Pd(OAc)2 (1.02 g) were added 396 mL of 1 N LHMDS in hexanes, then 400 mL of toluene under N2. The solution was cooled to −10° C. and tButyl acetate (49 mL was added. The solution was stirred at −10° C. for 10 min and was added 2-bromo-5-fluoro toluene. The mixture was heated at 80° C. for 15 min and was washed with NH4Cl and NaCl, dried with Na2SO4, filtered and concentrated. The crude was purified by flash chromatorghy with EtOAc/hexanes=1:30 to give tert-butyl (4-fluoro-2-methylphenyl)acetate (21.85 g).
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