Triethyl borate → HCID 43145275, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-bromo-2-(isopentyloxy)benzene (9.68 g, 40 mmol) in THF (160 mL) under N2 atmosphere at −78° C. was added dropwise n-butyl lithium (1.6 M in hexanes, 26.3 mL, 42 mmol, Aldrich) over 30 min period. The reaction mixture was stirred for an additional 1 hour at −78° C., followed by the drop wise addition of triethyl borate (5.86 mL, 51 mmol). The cooling bath was removed, and the reaction was allowed to warm up to the room temperature then stirred for an additional 18 h at room temperature. The reaction mixture was acidified with 2 N HCl (20 mL) and water (50 mL). The resulting slurry was extracted with 5 of 80 mL portions of Et2O. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure to give 6.30 g (77%) of 2-(isopentyloxy)-phenylboronic acid. 1H NMR (400 MHz, CDCl3): 7.83 (d, 1H), 7.43 (dd, 1H), 7.03 (t, 1H), 6.93 (t, 1H), 6.05 (s, 1H), 4.10 (t, 2H), 1.85-1.75 (m, 3H), 1.02 (s, 6H).

Provenance & Evidence