Hydrochloric Acid → 2-Methoxyphenylboronic acid

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence