Hydrochloric Acid → 4-(4-Methoxymethylcyclohexyl) phenyl boric acid

To a mixture of 4-(4-methoxymethylcyclohexyl)-1-iodobenzene (297 mmol) and 250 ml of THF, was added dropwise 200 ml of a solution of n-butyl lithium (corresponding to 312 mmol) in hexane at −78° C. in 3.0 hours, and stirred at the same temperature for 1.2 hours. To the solution was added dropwise 100 ml of a solution of triisopropyl borate (594 mmol) in THF, the solution was gradually warmed up to room temperature, and then the solution was stirred overnight. After 270 ml of 7.3% hydrochloric acid was added and stirred for 30 min, the reaction solution was extracted twice with diethyl ether, washed thrice with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was washed with heptane to give a white solid of 4-(4-methoxymethylcyclohexyl) phenyl boric acid (60.1 mmol).

1. stirringthe solution was stirred overnight
2. stirringstirred for 30 min
3. extractionthe reaction solution was extracted twice with diethyl ether
4. washwashed thrice with water
5. dry with materialdried over anhydrous magnesium sulfate
6. distillationThe solvent was distilled off
7. washthe residue was washed with heptane

ORD record

ord-c94d19fb7a934133a866d8ea8565273f

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06174458B1