Hydrochloric Acid → 4-Methylphenyl dihydrogen borate

To a mixture of 4-bromotoluene (743 mmol) and 500 ml of THF was added dropwise 500 ml of a solution of n-butyl lithium (corresponding to 780 mmol) in hexane at −78° C. in 1.6 hours, and stirred at the same temperature for 1.5 hours. To this solution was added dropwise 200 ml of a solution of triisopropyl borate (1,486 mmol) in THF, the solution was gradually warmed up to room temperature, and then the solution was stirred overnight. After 750 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 then dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was recrystallized from about 1,000 ml of toluene to give a white solid of 4-methylphenyl boric acid (545 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. customthe residue was recrystallized from about 1,000 ml of toluene

ORD record

ord-2df1c35f71304e74ad60b2e0e8e4585f

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06174458B1