[Li]CCCC.Br[C:7]1[CH:11]=[CH:10][S:9][CH:8]=1.[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.[NH4+].[Cl-]>C1COCC1>[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]([C:7]2[CH:11]=[CH:10][S:9][CH:8]=2)[OH:18])=[CH:15][CH:14]=1To a solution of 1.5M BuLi in hexanes (3.5 mL, 5.25 mmol) in THF (6.5 mL) cooled to −78° C. was added 3-bromothiophene dropwise (469 μL, 5.0 mmol). The mixture was stirred for 30 minutes and a 1.0M solution of 4-bromobenzaldehyde in THF was slowly added (5.5 mL, 5.5 mmol). The reaction was warmed to 0° C. and aged for 1 hour. The mixture was then poured into a saturated aqueous solution of NH4Cl. The resulting mixture was extracted 3 times with ethyl acetate and the organic layers were washed with brine, dried and evaporated. The crude residue was chromatographed on silica gel using a gradient of 10-25% ethyl acetate in hexanes to afford the title compound.
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