[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[O:13])[CH2:10][C:11]#[N:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:14](=S)=[S:15].[H-].[Na+].CI.[CH3:21][S:22]([CH3:24])=O>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[C:9]([C:10](=[C:21]([S:15][CH3:14])[S:22][CH3:24])[C:11]#[N:12])=[O:13]To a solution of 3-(3,4-dichlorophenyl)-3-oxopropanenitrile (3.3 g, 15.4 mmol) and carbon disulfide (0.927 mL, 15.4 mmol) in DMSO (50 mL) under an atmosphere of argon at 15° C. was added sodium hydride (0.856 g, 033.9 mmol) with vigorous stirring. The reaction mixture was stirred at this temperature for 10 min and was allowed to warm to rt. To the reaction mixture was added methyl iodide (1.92 mL, 30.8 mmol) and the mixture was stirred at rt for 30 min. The reaction mixture was diluted with water and extracted with EtOAc. The organic solutions were combined, washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography to give 2-(3,4-dichlorobenzoyl)-3,3-bis(methylsulfanyl)acrylonitrile (2.9 g, 59%). LCMS: (FA) ES-318.1. 1H NMR (400 MHz, CDCl3) δ: 7.95 (d, 1H), 7.73 (dd, 1H), 7.56 (d, 1H), 2.82 (s, 3H) and 2.55 (s, 3H).
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