Hydrochloric Acid → 4-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride)

Temperature

-78 °C

1-bromo-4-(octyloxy)benzene (14.64 g, 51.3 mmol) was dissolved in dry tetrahydrofuran in nitrogen atmosphere and cooled to −78° C. Butyllithium (50 ml, 80.0 mmol) was then added drop wise and the reaction mixture was let to room temperature. After an hour the mixture was once again cooled to −78° C. and triethylborate (23.6 g, 0.162 mol) was added drop wise. The reaction mixture was stirred over night at room temperature, acidified with 2M HCl, and the organic phase was recovered. It was washed once with water and three times with 1M sodium hydroxide to form a white soapy solid. The combined alkaline phases were acidified with 2M HCl and extracted with ether three times. The combined ether phases were washed with water and dried over magnesium sulphate. The product precipitated in dichloromethane from the reduced ether phase to yield 4-(octyloxy)phenylboronic acid (7.15 g, 28.6 mmol) as a white solid.

1. customwas let to room temperature
2. temperatureAfter an hour the mixture was once again cooled to −78° C.
3. customthe organic phase was recovered
4. washIt was washed once with water and three times with 1M sodium hydroxide
5. customto form a white soapy solid
6. extractionextracted with ether three times
7. washThe combined ether phases were washed with water
8. dry with materialdried over magnesium sulphate
9. customThe product precipitated in dichloromethane from the reduced ether phase

ORD record

ord-be617dd875f04f31bf9d8631334c2454

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09343198B2