Hydrochloric Acid → 2-Methoxyphenylboronic acid

Temperature

0 °C

Anisole (2.16 g, 20.0 mmol) was dissolved in dry THF (50 ml) in a dry 100 ml flask flushed with nitrogen. The mixture was chilled in a dry ice/2-propanol bath, n-butyl lithium (10.9 ml of a 2.3M solution in hexanes, 25 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 (2.3 ml, 20 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 2.88 g (95%) of 2-methoxybenzene boronic acid as a clear oil which was used in the next step without further purification.

1. customflushed with nitrogen
2. temperatureThe mixture was chilled in a dry ice/2-propanol bath
3. additionn-butyl lithium (10.9 ml of a 2.3M solution in hexanes, 25 mmol) was added
4. customthe cooling bath was exchanged for an ice-water bath
5. stirringthe mixture was stirred at room temperature overnight
6. additionmixed well for 30 minutes
7. extractionextracted with ether (3×15 ml)
8. dry with materialdried (MgSO4)
9. concentrationconcentrated under reduced pressure which

ORD record

ord-596483055dbe4d20b75ae87a4f991084

Source dataset

uspto-grants-1995_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05444050