Potassium Carbonate → (4-((2-Methoxyethyl)thio)phenyl)boronic acid

Temperature

25 °C

To a solution of 4-mercaptophenylboronic acid (3.08 g, 20 mmol) in anhydrous N,N-dimethylormamide (50 mL) was added solid potassium carbonate (9.7 g, 70 mmol). The mixture was stirred at 25° C. for 10 min and then treated with 1-bromo-2-methoxy-ethane (6.6 mL, 70 mmol) dropwise. The resulting mixture was stirred at 25° C. for 7 h and quenched with water. The mixture was extracted with ethyl acetate (2×150 mL), washed with water (3×100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 4-(2-methoxy-ethylsulfanyl)-phenylboronic acid (4 g, 94%) which was used in the next step without further purification.

1. stirringThe resulting mixture was stirred at 25° C. for 7 h
2. customquenched with water
3. extractionThe mixture was extracted with ethyl acetate (2×150 mL)
4. washwashed with water (3×100 mL)
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated in vacuo

ORD record

ord-c3b49017fb274a8f8366763f0eea211c

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08222416B2