5-bromo-2-prop-2-enoxyaniline

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

Procedure: A mixture of Example 66A (5.06 g, 19.69 mmol), iron powder (11.02 g, 196.9 mmol), NH4Cl (0.53 g, 9.85 mmol), ethanol (160 mL), and water (40 mL) were heated at 80° C. for 6 hours. The solution was filtered, concentrated with silica gel powder (18 g), and purified by flash chromatography eluting with 10% ethyl acetate in hexanes (1 L) to give the title compound (4.53 g, 97%). MS (DCI) m/z 227.91 (M+H)+; 1H NMR (300 MHz, CDCl3) δ ppm 4.54 (d, J=5.43 Hz, 2 H) 5.29 (dd, J=10.51, 1.36 Hz, 1 H) 5.40 (dd, J=17.46, 1.53 Hz, 1 H) 6.09 (m, 1 H) 6.65 (d, J=8.48 Hz, 1 H) 6.84 (m, 1 H) 6.91 (d, J=2.37 Hz, 1 H). The solution was filtered concentrated with silica gel powder (18 g) purified by flash chromatography eluting with 10% ethyl acetate in hexanes (1 L)