Hydrochloric Acid → 2-Methoxyphenylboronic acid

Temperature

-78 °C

Part B: Anisole (1.0 g, 9.25 mmol) was dissolved in dry THF (40 ml) in a dry 100 ml flask flushed with nitrogen and cooled to -78° C. n-Butyl lithium (5.8 ml of a 1.9M solution in hexanes, 11.1 mmol) was added then the cooling bath was exchanged for an ice-water bath. The reaction was stirred for an hour at 0° C. then trimethyl borate (1.26 ml, 10 mmol) was added and the mixture was stirred at room temperature overnight. The reaction mixture was treated with 2N aqueous HCl to pH 3 and mixed well for 30 minutes, then extracted with ether (3×15 ml). The organic materials were combined, dried (MgSO4) then concentrated under reduced pressure which gave 1.32 g (87%) of 2-methoxybenzeneboronic acid as a clear oil.

1. customflushed with nitrogen
2. additionwas added
3. customthe cooling bath was exchanged for an ice-water bath
4. stirringthe mixture was stirred at room temperature overnight
5. additionmixed well for 30 minutes
6. extractionextracted with ether (3×15 ml)
7. dry with materialdried (MgSO4)
8. concentrationthen concentrated under reduced pressure which

ORD record

ord-cdecfc7f85594ece8d8af6359d746dd2

Source dataset

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05622937