(3-(3-Methoxypropoxy)phenyl)boronic acid synthesis

Yield:-

Reaction Conditions:

Stage #1: 1-bromo-3-(3-methoxypropoxy)benzenewith n-butyllithium in tetrahydrofuran;hexane at -78; for 0.25 h;
Stage #2: with Triisopropyl borate in tetrahydrofuran;hexane at -78 - 20;
Stage #3: with hydrogenchloride;water in tetrahydrofuran;hexane;

Steps:

14.a

6.71 ml of n-butyllithium solution (1.6M in hexane) are added dropwise to a solution of 2.5 g of 1-bromo-3-(3-methoxypropoxy)benzene in 14 ml of dry tetrahydrofuran at -78°C. After stirring at this temperature for 15 minutes, 2.78 ml of triisopropyl borate are added, and the mixture is then slowly warmed to room temperature. 20 ml of 1 N HCl and 5 ml of conc. HCl are added to the reaction mixture, and the organic solvents are evaporated off in vacuo. The precipitate which has separated out is filtered off with suction and washed twice with ice-water. Drying under high vacuum affords 0.987 g of the title compound as a yellowish brown solid. Rt = 3.04.

References:

EP1987834,2008,A2 Location in patent:Page/Page column 34