Hydrochloric Acid → 3-Tolylboronic acid

Temperature

-78 °C

n-Butyllithium (15 mL, 2.5M in hexane, 37.4 mmol) was added dropwise to a solution of 3-bromotoluene (5.8 g, 34.0 mmol) in 50 mL of THF cooled to -78° C. The resulting suspension was stirred at -78° C. for 30 min, treated with trimethyl borate (10.6 g, 102.2 mmol), stirred -78° C. for 10 min, and allowed to warm to room temperature. The reaction mixture was stirred at room temperature for 16 hours, then cooled in an ice bath and acidified to pH 6 with 2N HCl. The mixture was extracted with methylene chloride, and the organic extract was washed with bdne, dried over Na2SO4, and concentrated to yield 4.24 g of 3-methylphenyl boronic acid.

1. stirringstirred -78° C. for 10 min
2. temperatureto warm to room temperature
3. stirringThe reaction mixture was stirred at room temperature for 16 hours
4. temperaturecooled in an ice bath
5. extractionThe mixture was extracted with methylene chloride
6. extractionthe organic extract
7. washwas washed with bdne
8. dry with materialdried over Na2SO4
9. concentrationconcentrated

ORD record

ord-98a493ce96a542098e635d408d90f790

Source dataset

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05597832