2-[2-(bromomethyl)phenyl]-1,3,2-dioxaborinane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of N-pyren-1-ylmethyl-hexane-1,6-diamine (291 mg, 0.69 mmol), 2-(2-bromomethyl-phenyl)-[1,3,2]dioxaborinane (422 mg, 1.66 mmol), and potassium carbonate (380 mg, 2.76 mmol) in dry acetonitril (10 ml) was heated at reflux for 20 hours under nitrogen atmosphere. The solvent was removed under vacuum, the residue was dissolved in chloroform and washed with water. The solvent was dried over magnesium sulphate and removed under vacuum. The residue was dissolved in THF (10 ml). Water (10 ml) was added to the THF solution, and the solution was stirred at room temperature for 3 hours. Organic phase was extracted with chloroform, washed with water, and dried over magnesium sulphate. The solvent was removed under vacuum. The residue was reprecipitated from chloroform with n-hexane to give a white yellow powder (172 mg, 35%). 1H NMR (CDCl3) δ/ppm 1.25-1.48 (8H, m, (CH2)4), 2.25 (2H, t, BnNCH2), 2.48 (2H, t, PyCNCH2), 3.45 (2H, s, PhB(OH)CH2NBn), 3.58 (2H, s, PhB(OH)CH2NCPy), 3.85 (2H, s, PhCH2), 4.21 (2H, s, PyCH2), 7.02-7.41 and 7.88-8.19 (22H m, Ar-H), 8.86 (4H, bs, BOH). 13C NMR (CDCl3) δ/ppm 51.69, 52.99, 54.42, 56.42, 57.11, 61.03, 61.86, 67.85, 122.90, 124.55, 124.99, 125.79, 127.31, 128.28, 128.57, 129.43, 130.00, 130.55, 136.32, 141.56; Found: C, 76.56; H, 6.69; N, 3.80, C44H46B2N2O4 requires C, 76.76; H, 6.73 N, 4.07%; m/z (FAB) 1230 ([M+H+4(3-HOCH2C6H4NO2)-4(H2O)]+, 100%); mp. 165-168° C. at reflux for 20 hours under nitrogen atmosphere The solvent was removed under vacuum the residue was dissolved in chloroform washed with water The solvent was dried over magnesium sulphate removed under vacuum The residue was dissolved in THF (10 ml) Water (10 ml) was added to the THF solution Organic phase was extracted with chloroform washed with water dried over magnesium sulphate The solvent was removed under vacuum The residue was reprecipitated from chloroform with n-hexane