Реакция #487421

Уравнение реакции

triethylborate

p-bromoanisole

sulfuric acid

water

→

expected product

(4-methoxyphenyl)-boronic acid

Растворители

ether

diethyl ether

diethyl ether

Условия реакции

Обработка

1. 1
   Температураthe mixture was refluxed for 2 hours
2. 2
   workup.WAITfor one hour at ambient temperature
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITwas carried out for one hour
5. 5
   ЭкстракцияThe organic phase was extracted with 100 ml of a saturated aqueous solution of sodium bicarbonate
6. 6
   Экстракцияfollowed by extraction with ether
7. 7
   Другоеdrying
8. 8
   Другоеevaporating under reduced pressure

Методика

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 6N hydrochloric acid, followed by extraction with ether, drying and evaporating under reduced pressure to obtain 3.9 g of the expected product.

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