Hydrochloric Acid → (4-Chloro-3,5-dimethoxyphenyl)boronic acid

Under an argon atomsphere, to dry THF (2 mL) stirred in a dry ice-methanol bath was gradually added a 1.57 M solution of n-butyllithium in hexane (0.8 mL), followed by the dropwise addition of a solution of 1-bromo-4-chloro-3,5-dimethoxybenzene (160 mg) in dry THF (2 mL). After the mixture was stirred for 20 minutes in the dry ice-methanol bath, triisopropyl borate (0.18 mL) was added and the mixture was additionally stirred for 20 minutes. The reaction mixture was then stirred at room temperature for 1 hour and pH of the mixture was adjusted at 3 using 4 M hydrochloric acid. The mixture was stirred at 0° C. for 1 hour and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated. The residue was recrystallized from ethyl acetate-hexane giving the title compound as white powder.

1. additionwas added
2. stirringThe reaction mixture was then stirred at room temperature for 1 hour
3. stirringThe mixture was stirred at 0° C. for 1 hour
4. extractionextracted with ethyl acetate
5. washThe organic layer was washed with brine
6. dry with materialdried over anhydrous sodium sulfate
7. customevaporated
8. customThe residue was recrystallized from ethyl acetate-hexane giving the title compound as white powder

ORD record

ord-087583d1a7aa40609d0b85caf102c688

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06605620B1