Ethyl chloroformate → (4-Bromo-2,6-dimethyl-phenyl)-carbamic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

4-Bromo-2,6-dimethyl-aniline (10 g), ethyl chloroformate (5.4 g) and potassium carbonate (10.4 g) were mixed in tetrahydrofuran (100 mL) and heated to reflux for 16 hours, cooled, filtered and concentrated in vacuo. Heptane (200 mL) was added to the crude product, which was stirred for 30 minutes at 70° C. The mixture was filtered and concentrated in vacuo to furnish 12 g (88% yield) of the title compound as a solid. LC-MS (m/z) 273 (MH+); tR=2.95, (UV, ELSD) 99%, 99%. 1H NMR (500 MHz, CDCl3): 1.31 (t, 3H), 2.24 (s, 6H), 4.19 (q, 2H), 5.92 (b, 1H), 7.22 (s, 2H).

Provenance & Evidence