Water → (4-Methoxyphenyl)boronic acid

Temperature

-70 °C

100 ml of a solution of 10 g of p-bromoanisole in anhydrous diethyl ether were added dropwise at reflux under an inert gas atmosphere to a suspension of 1.3 g of Mg turnings in 5 ml of anhydrous diethyl ether, and the mixture was refluxed for 2 hours. The mixture was then poured into a solution of 9.02 ml of triethylborate in 60 ml of anhydrous ether cooled to -70° C. After stirring for one hour at -70° C., then for one hour at ambient temperature, the solution was poured into a mixture of 11 ml of sulfuric acid and 50 g of ice and water and stirring was carried out for one hour. The organic phase was extracted with 100 ml of a saturated aqueous solution of sodium bicarbonate and the aqueous phases were combined and reacidified with 6 N hydrochloric acid, followed by extraction with ether, drying and evaporating under reduced pressure to obtain 3.9 g of the expected product.

1. temperaturethe mixture was refluxed for 2 hours
2. waitfor one hour at ambient temperature
3. stirringstirring
4. waitwas carried out for one hour
5. extractionThe organic phase was extracted with 100 ml of a saturated aqueous solution of sodium bicarbonate
6. extractionfollowed by extraction with ether
7. customdrying
8. customevaporating under reduced pressure

ORD record

ord-40f8ca293c6e4476a5dd87c6f41f742e

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05965763