o-Vanillin (99%, TCI America)
2-Bromoaniline (98%, TCI America)

In a tared 250 mL beaker, o-vanillin (0.76 g, 5.0 mmol) and 2-bromoaniline (0.82 g, 5.0 mmol) were mixed (using a glass-stirring rod) until an orange oil was formed; after 25 min, 50 mL of hexanes was added to the reaction mixture, which was transfered into a 100 mL round-bottom flask. After 24 hours, small needles of crystals appeared in the flask. The hexanes was removed by rotary evaporation to provide the dark orange solid (E)-2-(((2-bromophenyl)imino)methyl)-6-methoxyphenol (1.39 g, 4.5 mmol, 91% yield).

This compound was reluctant to become a solid. It was not recrystallized; all characterization was preformed on the crude product.

¹H NMR (400 MHz, CDCl₃): δ 13.56 (s, 1H, ArOH), 8.62 (s, 1H, N=CH), 7.68 (d, 1H), 7.37 (t, 1H), 7.26 (d, 1H), 7.15 (t, 1H),  7.03 (t, 2H), 6.90 (t, 1H), 3.95 (s, 3H, ArOCH₃).

¹³C NMR (100 MHz, CDCl₃): δ  162.97, 151.38, 148.54, 146.36, 133.32, 128.42, 128.10, 123.86, 120.26, 118.90 (2), 118.66, 114.89, 56.16.
IR (cm^–1): ν 3676, 2988, 2902, 1722, 1612, 1224
R_f 0.60 on SiO₂ in 1:9 ethyl acetate:hexane
M.p. 109-112°C

K.M. Touchette, J. Chem. Ed. 2006, 83 (6), 926. DOI: 10.1021/ed083p929

E. Hadjoudis, M. Vittorakis, I. Moustakali-Mavridis, Tetrahedron 1987, 43 (7), 1345. DOI: 10.1016/S0040-4020(01)90255-8