Dimethylformamide → HCID 58934969, compound

Participants

Reaction Conditions

Reaction Steps

To the mixture of 1.5 g (4.61 mmol) of ethyl 6-chloro-7-fluoro-2-(trifluoromethyl)-2H-chromene-3-carboxylate, 1.04 g (6.44mmol) of 2-chloro-4-bromophenol, and 0.89 g (8.76 mmol) potassium carbonate was added 10 mL of anhydrous DMF. The resulting mixture was heated to 110° C. for five hrs. After cooling to room temperature the reaction was treated with 150 mL of ethyl acetate. The organic phase was washed with saturated sodium bicarbonate three times and brine three times and dried over anhydrous magnesium sulfate. After removing the volatiles, the residue was purified on a silica gel column with EtOAc/hexane (1:9) to afford 1.8 g (76.3%) of a light yellow solid: 1H NMR (CDCl3/400MHz) 7.69(s, 1H), 7.68(s, 1H), 7.47 (dd,1H, J=2.4 Hz, 8.7 Hz), 7.37 (s, 1H), 7.00 (d, J=8.7 Hz, 1H), 6.38(s, 1H), 5.70(q, 1H, J=6.6 Hz), 4.35 (m, 2H), 1.38(t, 3H, J=7.2 Hz). MS (ESI+) 511 (M+1, 60), 513 (M+3, 100); HRMS (El) m/z calcd for (C19H12BrCl2F3O4) 509.9248, found 509.9274.

Provenance & Evidence