Acetic Acid → HCID 18782722, compound

Participants

Reaction Steps

4-Amino-2-bromoanisole (Desc. 4(a); 4.7 g) was dissolved in triethylorthoformate (50 ml), trifluoroacetic acid (1.8 ml) was added and the mixture heated at reflux for 48 hours. The solvent was removed in vacuo to afford a brown solid. Sodium azide (2.25 g) and acetic acid (25 ml) were added and the mixture heated at reflux for 6 hours. The product was purified on flash silica eluting with dichloromethane containing increasing proportions of methanol (0.25%, 0.5 and 0.75%) to give the title compound as a brown solid (3.98 g, 67% yield); δH (250MHz, DMSO-d6) 4.07 (3H, s, ArOCH3), 7.50 (1H, d, J 9Hz, 6-H), 8.03 (1H, dd, J 3, 9Hz, 5-H), 8.32 (1H, d, J 3Hz, 3-H), 10.16 (1H, s, 5'-H).

Provenance & Evidence