Triisopropyl borate → HCID 67209066, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(1-adamantyl)-4-benzyloxy-5-methoxyphenyl bromide (2.85 g, 6.67 mmol) in THF (12 mL) at −78° C. (dry ice/acetone bath) under argon was added 1.6 M n-BuLi (10.7 mmol) in hexane (6.67 mL) in one portion. This mixture was stirred at −78° C. for 15 min. Tri(isopropyl) borate (4.60 mL, 20.0 mmol) was added next, and the resulting solution was stirred at −78° C. for 20 min before being allowed to warm to room temperature with stirring overnight. The mixture was quenched with 1 N HCl (40 mL) and then extracted with EtOAc (100 and 60 mL). The combined organic extracts were washed with brine and dried. Solvents were removed at reduced pressure, and the residue was washed with hexane and dried to give 2.3 g (88%) of 3-(1-adamantyl)-4-benzyloxy-5-methoxyphenylboronic acid as a cream solid, mp 148-151° C. IR 3219, 2903, 2848, 1410, 1340, 1201 cm−1; 1H NMR (CDCl3) δ 1.72 (bs, 6H, AdCH2), 2.03 (bs, 3H, AdCH), 2.17 (m, 6H, AdCH2), 3.99 (s, 3H, OCH3), 5.21 (s, 2H, C6H5CH2), 7.31-7.58 (m, 5H, C6H5), 7.68 (d, J=1.4 Hz, 1H, 6-ArH), 7.92 ppm (d, J=1.4 Hz, 1H, 2-ArH).

Provenance & Evidence