4-Bromo-2,6-xylidine → N-(4-bromo-2,6-dimethyl-phenyl)-2-cyclopentyl-acetamide

Participants

Reaction Conditions

Reaction Steps

4-Bromo-2,6-dimethylaniline (5.92 g) and cyclopentylacetyl chloride (4.87 mL) were dissolved in acetonitrile (26 mL) and heated to 150° C. for 10 minutes in a sealed microwave process vial. The reaction was cooled to 0° C., the product filtered off and washed with cold acetonitrile (50 mL) affording 8.43 g (92% yield) of the title compound as a brown solid. The crude product was used without further purification. LC-MS (m/z) 312 (MH+); tR=3.10, (UV, ELSD) 89%, 99%. 1H NMR (500 MHz, CDCl3): 1.22 (m, 2H), 1.52 (m, 2H), 1.63 (m, 2H), 1.77 (m, 2H), 2.06 (s, 6H), 2.31 (m, 1H), 2.64 (d, 2H), 7.15 (s, 2H), 9.98 (b, 1H).

Provenance & Evidence