[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH:7]([C:12](OCC)=O)[C:8]2=[O:11])=[CH:4][C:3]=1[O:17][CH3:18].C([O-])([O-])=O.[K+].[K+].BrC[CH2:27][F:28].[OH-].[Na+]>CC(N(C)C)=O.C1COCC1.O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH:7]([CH2:12][CH2:27][F:28])[C:8]2=[O:11])=[CH:4][C:3]=1[O:17][CH3:18]To a solution of ethyl 6-chloro-5-methoxy-1-oxoindane-2-carboxylate (crude product from the preceding step, ˜141 mmol) in anhydrous dimethylacetamide (540 mL) was added K2CO3 (39 g, 282 mmol), KI (46.8 g, 282 mmol) and 1-bromo-2-fluoroethane (13.5 mL, 183 mmol) and the mixture was stirred and heated at 65° C. for 6 hours. The reaction mixture was diluted with THF (540 mL) and water (540 mL) and then cooled to 0° C. and treated with 5N aqueous NaOH (84 mL, 423 mmol). After 2 hours at 0° C., the reaction was quenched with 1N aqueous HCl (˜450 mL). Most of the THF was removed by rotary evaporation under reduced pressure and the aqueous residue was extracted with EtOAc. The organic layer was washed with saturated NaHCO3, dried over MgSO4, filtered through a pad of silica gel and concentrated to give 6-chloro-2-(2-fluoroethyl)-5-methoxyindan-1-one.
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