C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:25]I.[F:27][C:28]1[CH:40]=[CH:39][C:31]([CH2:32][O:33][CH2:34][CH:35]=[CH:36][CH2:37]O)=[CH:30][C:29]=1[CH3:41].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[F:27][C:28]1[CH:40]=[CH:39][C:31]([CH2:32][O:33][CH2:34][CH:35]=[CH:36][CH2:37][I:25])=[CH:30][C:29]=1[CH3:41]To a solution of triphenylphosphine (2.6 g, 9.9 mmol) in anhydrous 40 mL DCM was added imidazole (1.4 mg, 20.4 mmol) and iodine (2.5 mg, 9.9 mmol) at 0° C. The reaction mixture was stirred for 30 min at 0° C. and then 4-(4-Fluoro-3-methylbenzyloxy)but-2-en-1-ol (1.3 g, 6.2 mmol) in 10 mL DCM was added to the mixture. The resulting mixture was stirred at 0° C. for 2 h and the temperature was slowly raised to room temp over a period of 2 h. 20 mL of 10% sodium thiosulfate was added and extracted with more DCM (3×30 mL). The combined DCM layer was washed with brine (2×30 mL) and dried over sodium sulfate. Evaporation of solvent left the crude product as an oil from which the product was isolated by Flash column chromatography eluting with 0% to 10% ethyl acetate/hexane to give the title compound, 1.5 g, as a light yellow oil.
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