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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1642843Generated: November 1, 2026

Hydrochloric Acid → (3-Methyl-4-(trifluoromethoxy)phenyl)boronic acid

https://huagongshe.com/reaction/1642843

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantBoronic acid, methyl-, dimethyl esterHCID 138991—
Reactant4-Bromo-2-methyl-1-(trifluoromethoxy)benzeneHCID 40427090—
ReactantButyllithiumHCID 178418339—
SolventTetrahydrofuranHCID 8028—
SolventHexaneHCID 8058—
Product(3-Methyl-4-(trifluoromethoxy)phenyl)boronic acidHCID 46739138—

Reaction Conditions

Temperature-78 °C

Reaction Steps

At −78° C., 8.5 ml (1.4 g, 21.1 mmol) of a 2.5M solution of n-butyllithium in hexane were initially charged in 30 ml of THF. 4.9 g (19.2 mmol) of 4-bromo-2-methyl(trifluoromethoxy)benzene were dissolved in 15 ml of THF and slowly added dropwise. 3.0 g (28.8 mmol) of trimethylboronic acid were then added dropwise. The mixture was stirred at −78° C. for 2 h, and 11 ml of 2 N hydrochloric acid were then added. The mixture was allowed to warm to RT, and the organic phase was separated off. The solvent was removed under reduced pressure and the residue was recrystallized from n-heptane. Yield: 3.3 g (78% of theory)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08119663B2
Source datasetuspto-grants-2012_02
ORD IDord-0da5d26347384892a7b5f5213e6d0206
Source noteuspto-grants-2012_02