[Br:1][C:2]1[S:6][C:5]([C:7](O)([CH3:9])[CH3:8])=[N:4][CH:3]=1.[SH:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15]>ClCCCl.O.[I-].[Zn+2].[I-]>[Br:1][C:2]1[S:6][C:5]([C:7]([S:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])([CH3:9])[CH3:8])=[N:4][CH:3]=1
The product of Step 2 (9.00 g, 40.5 mmol) was taken up in 1,2-DCE (400 mL) before adding methyl 3-mercaptopropionate (9.74 g, 81 mmol) and zinc iodide (38.8 g, 122 mmol). The reaction was stirred at reflux for 5 h. The suspension was diluted with water and extracted with dichloromethane (2×). The combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated. Flash chromatography (0-15% ethyl acetate in hexanes) provided methyl 3-{[2-(5-bromo-1,3-thiazol-2-yl)propan-2-yl]sulfanyl}propanoate (12.58 g, 96%) as a colorless oil. ESI: [M+H]+ m/z 323.9/326.0.
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