[H-].[Na+].[CH:3]1([SH:8])[CH2:7][CH2:6][CH2:5][CH2:4]1.[Br:9][C:10]1[CH:11]=[C:12]([CH:16]=[C:17](Br)[CH:18]=1)[C:13]([OH:15])=[O:14].Cl>CS(C)=O.O>[Br:9][C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([S:8][CH:3]2[CH2:7][CH2:6][CH2:5][CH2:4]2)[CH:18]=1)[C:13]([OH:15])=[O:14]To a stirred mixture of sodium hydride (60% in mineral oil, 0.82 g, 20.5 mmol) and DMSO (15 mL) in a sealable flask at 0° C. was slowly added cyclopentanethiol (1.23 mL, 11.9 mmol). The mixture was stirred at room temperature for 30 min and then a solution of 3,5-dibromobenzoic acid (2.5 g, 8.9 mmol) in DMSO (10 mL) was added. The reaction was sealed and stirred at 80° C. overnight. After cooling, the reaction mixture was poured into water and adjusted to pH 5-6 with 15% HCl (aq.) and extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated to afford the crude product which was used for the next step reaction without further purification.
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