Dimethylformamide → 5-bromo-1-(4-hydroxyphenyl)-2-methyl-1H-indole-3-carbaldehyde

Participants

Reaction Steps

Phosphorous oxychloride (2.5 mL) was added to anhydrous dimethylformamide (5 mL) and stirred at room temperature for 15 min whereupon a solution of 5-bromo-1-(4-methoxymethyloxyphenyl)-2-methyl-1H -indole (0.65 g, 1.9 mmol) in dimethylformamide (10 mL) was added. The solution was reacted according to the procedure used in Example 2a to afford a tan solid (51%): mp>250° C.; 1H NMR (DMSO-d6): δ 2.50 (3H, s), 6.95-7.02 (3 H, m), 7.21 (1H, dd, J=2.4 Hz, J=8.8 Hz), 7.28 (2H, d, J=8.7 Hz), 8.38 (1H, d, J=2.2 Hz), 9.98 (1H, s), 10.14 (1H, s); MS m/Z (M+H)+ 318/320 (1 Br). Anal. for C16H12BrNO2·0.2H2O: Calc'd: C, 55.99; H, 3.88; N, 4.35. Found: C, 55.69; H, 3.95; N, 4.15.

Provenance & Evidence