2,3,4,5-tetramethoxybenzaldehyde

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to a general aryl chlorination procedure by Lopez-Alvarado,39 19 (0.767 g, 3.39 mmol) was dissolved in CH2Cl2 (10.0 mL) at room temperature and then SO2Cl2 (neat, 0.31 mL, 3.7 mmol) was added at room temperature. The reaction was stirred for 1 hour and monitored by 1H NMR for completion. The reaction was then diluted with CH2Cl2, washed with brine, dried over MgSO4, filtered, and condensed. The resulting oil was then purified by flash column chromatography (1:4 Et2O:hexanes) to provide 20 (0.861 g, 3.30 mmol, 97%) as a colorless oil. washed with brine dried over MgSO4 filtered condensed The resulting oil was then purified by flash column chromatography (1:4 Et2O:hexanes)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the procedure by Syper et al.,19 N-methylformanilide (1.0 mL, 8.1 mmol) was added to a flame dried 10 mL round bottom flask under argon and a drying tube. POCl3 (1.0 mL, 11 mmol) was added at room temperature and the Argon line was removed. After 5 minutes 18 (1.067 g, 5.38 mmol) was dissolved in CH2Cl2 (2.0 mL) and added at room temperature. The reaction was stirred at room temperature under a drying tube for 48 hrs and monitored by 1H NMR. When complete the reaction was diluted with EtOAc, washed with saturated brine, dried over MgSO4, filtered, and condensed. The resulting product was separated from remaining N-methylformanilide using flash chromatography (1:4 Et2O:hexanes) to provide 19 (1.141 g, 5.04 mmol, 94%) as a colorless oil. was added to a flame dried 10 mL round bottom flask under argon the Argon line was removed added at room temperature washed with saturated brine dried over MgSO4 filtered condensed The resulting product was separated