[CH3:1][C:2]([S:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[Br:8][C:9]1[C:10]2[CH:20]=[CH:19][CH:18]=[CH:17][C:11]=2[S:12][C:13]=1[C:14](=O)[CH3:15]>C1COCC1.[Cl-].[Na+].O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Br:8][C:9]1[C:10]2[CH:20]=[CH:19][CH:18]=[CH:17][C:11]=2[S:12][C:13]=1/[C:14](=[N:7]/[S:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])/[CH3:15]
A mixture of titanium (IV) ethoxide (2.272 mL, 10.97 mmol), 2-methyl-2-propane-sulfinamide (0.665 g, 5.49 mmol) and 1-(3-bromobenzo[b]thiophen-2-yl)ethanone (1.40 g, 5.49 mmol) in THF (15 mL) was heated to reflux overnight. After 24 h, the reaction was equilibrated to rt and poured into 100 mL of brine. The solid was removed by filtration through celite and the pad was rinsed with 100 mL of EtOAc. The organic layer was stirred over MgSO4, filtered and concentrated under reduced pressure to give an orange oil. The product was purified by column chromatography on a silica column using 20 to 40% gradient of EtOAc-hexane as eluent to give (E)-N-(1-(3-bromobenzo[b]thiophen-2-yl)ethylidene)-2-methylpropane-2-sulfinamide as an orange oil: 1H NMR (400 MHz, CDCl3) δ 1.34 (s, 9H), 2.98 (s, 3H), 7.35-7.45 (m, 2H), 7.65-7.73 (m, 1H), 7.83 (dd, J=7.3, 2.1 Hz, 1H).
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