Hydrochloric Acid → (5-Methylthiophen-2-yl)boronic acid

To a stirred solution of 2-bromo-5-methylthiophene (2.5 g, 14.1 mmol) in THF (30 mL) was added n-BuLi (1.55 M solution in hexane, 10.0 mL, 15.5 mmol) at −78° C. under nitrogen, and the mixture was stirred for 1 hour. Trimethylborate (1.83 g, 17.6 mmol) was added to the mixture, and residue was allowed to warm up to room temperature overnight. The reaction mixture was cooled at 0° c and 2N HCl (10 mL) was added, and the mixture was stirred for 1 hour. The organic layer was separated and the aqueous layer was extracted with diethylether. The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo, to give the title compound (1.36 g).

1. additionwas added
2. stirringthe mixture was stirred for 1 hour
3. customThe organic layer was separated
4. extractionthe aqueous layer was extracted with diethylether
5. washThe combined organic layer was washed with brine
6. dry with materialdried over MgSO4
7. concentrationconcentrated in vacuo

ORD record

ord-0cb2544ca0b44929ac5ba89ca80db0a8

Source dataset

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06949536B2