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ChemicalBook CAS DataBase List 4-(Phenoxycarbonylamino)benzeneboronic acid pinacol ester, 95%
756520-47-5

4-(Phenoxycarbonylamino)benzeneboronic acid pinacol ester, 95% synthesis

2synthesis methods
-

Yield:756520-47-5 91%

Reaction Conditions:

with pyridine in dichloromethane; for 13 h;Heating / reflux;

Steps:

10.1

4-(4,4,5,5-tetramethyl 1,3,2 dioxaboralan-2-yl) aniline (3 g, 0.013 mol) was dissolved in dichloromethane (350 mL) to which pyridine (1.02 g, 0.013 mol) and 4-nitrophenyl chloroformate was added. The reaction was stirred for 13 hr where TLC analysis showed consumption of all starting materials. The solution was washed with saturated NaHCO3 (3x50 mL), water (3x50 mL) and brine (3x50 mL). The organic layer was dried over Na2SO4 and solvent removed to yield a white crystalline solid [4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-carbamic acid phenyl ester, 4.45 g, 91%. 1H NMR (CDCl3 300 MHz) ? 1.4 (s, 12H), 7.1 (brs, 1H), 7.3 (d, 2H), 7.5 (d, 2H), 7.8 (d, 2H), 8.3 (d, 2H).

References:

US2006/46991,2006,A1 Location in patent:Page/Page column 28