[F:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[C:17]([OH:18])=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:13]3)=[O:7])=[CH:4][CH:3]=1.CI.[C:27](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[F:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[C:17]([O:18][CH3:27])=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:13]3)=[O:7])=[CH:4][CH:3]=1A mixture of 5-(4-fluorobenzoyl)-6-hydroxy-2-methylsulfonylnaphthalene (1.0 g, 2.9 mmol), [prepared as described in step 3 above], methyl iodide (0.65 ml, 10.45 mmol), and potassium carbonate (0.64 g, 4.65 mmol) in N,N-dimethylformamide (10 ml) was stirred at room temperature. After 16 h, the reaction mixture was diluted with water and extracted into ethyl acetate. The organic layer was separated, washed with brine, and dried over sodium sulfate. The solvent was removed in vacuo and the crude product was purified by flash chromatography (gradient elution 40-100% ethyl acetate/hexanes) to give 1.0 g of 5-(4-fluorobenzoyl)-6-methoxy-2-methylsulfonylnaphthalene as a solid (96% yield).
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