[Si]([O:8][C:9]1[C:10]([F:18])=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=[O:13])(C(C)(C)C)(C)C.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH2:27](Cl)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C=O)C.O>[CH2:27]([O:8][C:9]1[C:10]([F:18])=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([O:14][CH2:12][C:11]1[CH:15]=[CH:16][CH:17]=[CH:9][CH:10]=1)=[O:13])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1
To a mixture of 3-tert-butyldimethylsilyloxy-2-fluorobenzoic acid (7.74 g, 29 mmol), potassium carbonate (24.0 g, 174 mmol) and sodium iodide (25.9 g, 174 mmol) in DMF (180 ml) was added benzyl chloride (8.33 ml, 72.4 mmol) dropwise over 5 min. After stirring for 2 days the reaction mixture was poured into water (400 ml) and extracted with diethyl ether (3×200 ml). The combined extracts were washed with brine (100 ml), dried (MgSO4) and concentrated under reduced pressure. The crude product obtained was recrystallized from 2-propanol to afford title compound (7.19 g, 74%) as white flakes.
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