[Li+].CC([N-]C(C)C)C.[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]2[CH:21]=[CH:20][S:19][CH:18]=2)=[CH:12][CH:11]=1.[I:22]I>C1COCC1>[I:22][C:20]1[S:19][CH:18]=[C:17]([CH2:16][C:13]2[CH:12]=[CH:11][C:10]([F:9])=[CH:15][CH:14]=2)[CH:21]=1To a solution of LDA (3.67 mmol) in THF at -78° C. was added a solution of 3-(4-fluorophenylmethyl)thiophene (640 mg, 3.33 mmol), prepared as in Example 35, step 1, and the reaction mixture was stirred for 25 min. A solution of I2 (1.01 g, 4.00 mmol) in THF was added and the cold bath was removed. The reaction mixture was warmed to ambient temperature, quenched with saturated aqueous NH4Cl, and extracted with ether. The organic phase was washed with 1N aqueous H3PO4, saturated aqueous NaHCO3, saturated aqueous Na2S2O3, and brine, dried over MgSO4, filtered, and concentrated in vacuo to give 928 mg of 2-iodo-4-(4-fluorophenylmethyl)thiophene which was used without further purification.
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