Triisopropyl borate → 3-(1-Adamantyl)-4,5-methylenedioxyphenylboronic acid

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To a solution of 4-(1-adamantyl)-6-bromobenzo[1,3]dioxole (2.10 g, 6.26 mmol) in THF (11 mL) at −78° C. (dry ice/acetone bath) under argon was added 1.6 M n-BuLi (10.0 mmol) in hexane (6.26 mL) in one portion. This mixture was stirred at −78° C. for 15 min. Tri(isopropyl)borate (4.30 mL, 18.8 mmol) was added, and the resulting solution was stirred at −78° C. for 20 min more 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 40 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 1.23 g (65%) of 3-(1-adamantyl)-4,5-methylenedioxyphenylboronic acid as a cream solid, mp 258-261° C. IR 3231, 2903, 2849, 1343, 1164 cm−1; 1H NMR δ (CDCl3) 1.81 (bs, 6H, AdCH2), 2.13 (bs, 9H, AdCH2 and AdCH), 6.02 (s, 2H, CH2), 7.48 (s, 1H, 6-ArH), 7.75 ppm (s, 1H, 2-ArH).

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