[1,1'-Biphenyl]-2-ol, 4'-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)- synthesis

Yield:1467061-56-8 99%

Reaction Conditions:

in 1,4-dioxane at 210; for 1 h;Microwave irradiation;

Steps:

101.1 4'-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)-[1,1'-biphenyl]-2-ol

A mixture of 2,2-dimethylpropane-1,3-diol (4.0 g, 38 mmol) and 4'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-ol (1.0 g, 3.4 mmol) in 1,4-dioxane (2 mL) was subjected to microwave irradiation at 210° C. for 1 hour.
The cooled reaction mixture was partitioned between water (50 mL) and 1:1 EtOAc/heptane (25 mL:25 mL).
The organic layer was washed with water (30 mL) and brine (30 mL), dried over Na₂SO₄ and concentrated in vacuo to give the title compound (0.95 g, 99% yield). GC/MS, M=282 at 5.31 min. ¹H NMR (500 MHz, CDCl₃) δ 7.94 (d, J=7.81 Hz, 2H), 7.48 (d, J=7.81 Hz, 2H), 7.31-7.26 (m, 2H), 7.03-6.98 (m, 2H), 3.82 (s, 4H), 1.08-1.04 (m, 6H).

References:

US2013/267493,2013,A1 Location in patent:Paragraph 1148