Water → (2,6-Dimethoxyphenyl)boronic acid

Temperature

-78 °C

1,3-Dimethoxybenzene (4 g) was dissolved in freshly distilled THF (10 mL). This solution was cooled to −78° C. and n-BuLi (24 mL, 1.6 M solution in hexanes) was added dropwise to the cold solution. The mixture was stirred at −78° C. for 1 h, then warmed to room temperature and stirred for 1 h. The resulting mixture was cooled again to −78° C. and (MeO)3B (6.7 mL) was added. The mixture was allowed to warm to room temperature and stirred overnight. Water (10 mL) was added, and the mixture was stirred for 0.5 h, acidified to pH 4 with acetic acid and extracted with EtOAc. The extract was dried (MgSO4) and evaporated to give 2,6-dimethoxybenzeneboronic acid, which was used without further purification.

1. temperaturewarmed to room temperature
2. stirringstirred for 1 h
3. temperatureThe resulting mixture was cooled again to −78° C.
4. temperatureto warm to room temperature
5. stirringstirred overnight
6. stirringthe mixture was stirred for 0.5 h
7. extractionextracted with EtOAc
8. dry with materialThe extract was dried (MgSO4)
9. customevaporated

ORD record

ord-d59ade9a59d241b4931c9e0bd6130bdd

Source dataset

uspto-grants-2005_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06855843B2