Potassium Bromide → HCID 10220574, compound

Participants

Reaction Steps

In an oven-dried flask purged with argon, a solution of 4-bromo-2-chlorobenzonitrile (268 mg, 1.238 mmol), 2,6-difluorophenylboronic acid (293 mg, 1.857 mmol), Pd(PPh3)4 (143 mg, 0.124 mmol) in toluene (10 mL) and EtOH (10 mL), and saturated solution of NaHCO3 in water (1 mL) were refluxed while sterring for 5 h. The reaction mixture was poured into water and extracted 3 times with CH2Cl2. The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude compound was then purified by flash cromatography (diethyl ether-hexanes) to provide EM-4977 (45 mg, 15%) as a white solid. IR (KBr): 3072, 2237, 1626, 1602, 1578, 1468, 1386, 1231, 1058, 996, 888, 844, 783, 730, 693, 622, 516 cm−1. 1H RMN (400 MHz, acetone d6) δ 7.23 (t, J=8 Hz, 2H), 7.60 (m, 1H), 7.73 (ddd, J=1.3, 1.4 & 8 Hz, 1H), 7.88 (d, J=1.3 Hz, 1H), 8.07 (d, J=8 Hz, 1H) ppm. 13C RMN (75 MHz, CDCl3) δ 112.06 (d, J=25 Hz), 112.14, 112.85, 115.83, 129.15, 130.80 (t, J=11 Hz), 131.73, 133.63, 135.40, 136.70, 159.63 (dd, J=7 & 250 Hz) ppm. GC/NCI/MS (m/e); 249 (M−, 100).

Provenance & Evidence