Hydrochloric Acid → HCID 67326361, compound

Participants

Reaction Steps

To a solution of 3-fluoro-4-[4-formyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-benzonitrile (4) (8.23 g, 22.4 mmol) in MeOH (anhydrous, 150 mL) was added NaBH4 (2.56 g, 67.2 mmol) slowly. The reaction was stirred at room temperature for 2 hours, then 1 M HCl (50 mL) was slowly added. The reaction was stirred over night. The methanol was evaporated under vacuum. Much of white solid was formed during the evaporation. The solid was filtered, washed with water, and air-dried to afford 3-fluoro-4-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-6-yloxy)-benzonitrile (5) 4.5 g in 75% yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.24 (s, 1 H), 8.06 (dd, J=10.94, 1.95 Hz, 1 H), 7.67 (d, J=8.60 Hz, 1 H), 7.49 (d, J=8.21 Hz, 1 H), 7.36 (d, J=2.34 Hz, 1 H), 7.29 (dd, J=8.21, 2.34 Hz, 1 H), 7.13 (t, J=8.40 Hz, 1 H), 4.98 (s, 2 H). ESMS (m/z): 268 (M−H)−. HPLC: 95.27% (220 nm), 97.09% (254 nm), 97.20% (maxplot).

Provenance & Evidence