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Stage #1: 5-bromo-6-methoxy-1H-indole With diethylaluminium chloride In hexane; dichloromethane at 0℃; for 1h;
Stage #2: acetyl chloride In hexane; dichloromethane for 1h;
Stage #3: With citric acid In hexane; dichloromethane; water at 20℃; for 1h;
6.1 Step 1: 1-(5-Bromo-6-methoxy-1H-indol-3-yl)ethan-1-one (S2)
5-Bromo-6-methoxy-1H-indole (1.01 g, 4.47 mmol) in DCM (20 mL) was treated with Et2AlCl in hexane (1.0 M, 6.71 mL, 1.5 equiv) at 0° C. for 1 h. AcCl (0.479 mL, 6.71 mmol) in DCM (mL) was added and the reaction mixture was stirred for an additional 1 h. To this mixture was added 5% aq. citric acid (100 mL) and the reaction was stirred at room temperature for 1 h. The resulting brick-colored solid was collected by filtration and dried to give 1-(5-bromo-6-methoxy-1H-indol-3-yl)ethan-1-one (0.62 g).
0.62 g
Stage #1: 5-bromo-6-methoxy-1H-indole With diethylaluminium chloride In hexane; dichloromethane at 0℃; for 1h;
Stage #2: acetyl chloride In hexane; dichloromethane for 1h;
5.1 1-(5-Bromo-6-methoxy-lH-indol-3-yl)ethan-l-one
5-Bromo-6-methoxy-lH-indole (1.01 g, 4.47 mmol) in DCM (20 mL) was treated with Et2AlCl in hexane (1.0 M, 6.71 mL, 1.5 equiv) at 0 °C for 1 h. AcCl (0.479 mL, 6.71 mmol) in DCM (mL) was added and the reaction mixture was stirred for an additional 1 h. To this mixture was added 5% aq. citric acid (100 mL) followed by stirring at rt for 1 h. The resulting brick-colored solid was collected by filtration and dried to give l-(5-bromo-6-methoxy-lH-indol-3-yl)ethan-l- one (0.62 g).
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