Hydrochloric Acid → 2,6-Dimethylphenylboronic acid

A 1.0 M solution of 2,6-dimethylphenylmagnesium bromide in THF (20 ml; 20 mmol) was added over 5 minutes to a solution of trimethylborate (4.5 ml; 40 mmol) in 50 ml of THF at −78° C. The reaction mixture was allowed to warm to room temperature and stir 18 hr. Mter cooling to 0° C., 50 ml of 2 N HCl was added and the resulting mixture was stirred 30 minutes at 0° C. The mixture was partitioned between water (100 ml) and CH2Cl2 (100 ml). The aqueous layer was extracted with CH2Cl2 (2×100 ml) and the combined organic layers were dried (MgSO4) and concentrated to afford a quantitative recovery of the crude title compound of this step. This material was used in the next step without further purification.

1. temperatureMter cooling to 0° C.
2. stirringthe resulting mixture was stirred 30 minutes at 0° C
3. customThe mixture was partitioned between water (100 ml) and CH2Cl2 (100 ml)
4. extractionThe aqueous layer was extracted with CH2Cl2 (2×100 ml)
5. dry with materialthe combined organic layers were dried (MgSO4)
6. concentrationconcentrated

ORD record

ord-504ded53f2c4454e9784940d8259f5bf

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06235740B1