Dimethylformamide → HCID 67608705, compound

Participants

Reaction Steps

A solution of 3,4-difluoro-phenol (342 mg, 2.6 mmol) in DMF (5 mL) was treated with Cs2CO3 (1.0 g, 3.1 mmol). After 20 min, the yellow solution was treated with mesylate 79 (610 mg, 1.3 mmol) in DMF (5 mL). The reaction mixture was stirred at ambient temperature. After 16 h, the reaction mixture was heated at 60° C. for 3.5 h and then cooled to ambient temperature. The reaction mixture was diluted with Et2O and water. The layers were separated and the aqueous phase was extracted with Et2O. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by HPLC (2″ Dynamax® SiO2, 10% EtOAc/hexane to 100% EtOAc, 30 min; Flow: 40 mL/min) to afford the 78 (422 mg, 67%) as a light yellow-colored oil. 1H NMR (CDCl3, 300 MHz): δ7.37-7.28 (m, 5H), 7.05-7.03 (m, 1H), 6.66-6.64 (m, 1H), 6.54-6.51 (m, 1H), 5.18-5.09 (m, 2H), 4.49-4.47 (m, 1H), 4.24-4.16 (m, 1H), 3.99 (m, 0.5H), 3.81-3.69 (m, 3H), 3.62 (m, 0.5H), 3.55-3.49 (m, 1H), 3.25-3.16 (m, 1H), 2.87-2.74 (m, 1H), 2.26-2.12 (m, 1H), 1.99 (m, 1H), 1.49 (s, 9H) ppm.

Provenance & Evidence