[CH:1]([N-]C(C)C)(C)C.[Li+].[Br:9][C:10]1[CH:15]=[C:14]([S:16][CH3:17])[CH:13]=[C:12]([F:18])[CH:11]=1.IC.[Cl-].[Na+]>C1COCC1.C(C1C=CC=CC=1)C>[Br:9][C:10]1[CH:15]=[C:14]([S:16][CH3:17])[CH:13]=[C:12]([F:18])[C:11]=1[CH3:1]7.5 ml of a 2 M solution of lithium diisopropylamide in THF/HEP/ethylbenzene (Aldrich) were dissolved in 30 ml of anhydrous THF and cooled to −73° C. A solution of 3.0 g of 1-bromo-3-fluoro-5-methylsulfanylbenzene in 10 ml of anhydrous THF added at a temperature between −73° C. and −67° C. Stirring was continued for 90 min at −75° C., then 1.0 ml of iodomethane was added at this temperature. The mixture was then warmed up to room temperature, 100 ml of a saturated aqueous solution of sodium chloride were added and the mixture was extracted twice with 100 ml each of EA. The extracts were dried and concentrated in vacuo to yield 2.0 g of the title compound as a slight yellow oil that was used without further purification.
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