[Li]CCCC.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[C:15]([F:18])([F:17])[F:16].CN(CCN(C)C)C.CN([CH:30]=[O:31])C.Cl>C(OCC)C>[Cl:6][C:7]1[C:8]([C:15]([F:16])([F:17])[F:18])=[CH:9][C:10]([O:13][CH3:14])=[C:11]([CH:12]=1)[CH:30]=[O:31]A 1.61 M hexanes solution of n-BuLi (18.7 mL, 30.1 mmol) was added to a −78° C. diethyl ether solution (45 mL) of 1-chloro-4-methoxy-2-(trifluoromethyl)benzene (5.3 g, 25.1 mmol) and TMEDA (4.5 mL, 30.1 mmol). After 30 min at −78° C. the reaction was transferred to an ice bath and stirred at 0° C. After 5 min DMF (5.0 mL, 65.0 mmol) was added and the reaction was maintained in the ice bath. After 2 hrs at 0° C. 6 M aqueous HCl (aq) (17.0 mL, 102 mmol) was added and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with 4 M NaCl and 5 M K2CO3, dried (Na2SO4), and concentrated to yield the title compound, which was used in the next step without further purification.
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