Triisopropyl borate → 4-(Trifluoromethyl)phenylboronic acid

To a solution of 1 mL (7.1 mmol) of 4-trifluoromethylphenyl bromide (JRD Fluoro Chemical LTD) in 20 mL of THF at −78° C. in a nitrogen atmosphere was added 7.1 mL (8.5 mmol) of nBuLi (1.6 M in THF). After stirring for 30 min, 2.5 mL (10.65 mmol) of triisopropyl borate (Aldrich) was slowly added and the reaction mixture was slowly warmed to rt. After 1 h at rt, the reaction mixture was concentrated and redissolved in 10 mL of a mixture of acetic acid and H2O (2:1). After stirring for 3 h, the reaction mixture was concentrated and redissolved in 100 mL of ethyl acetate. The solution was washed with sat'd NaHCO3 solution, and the organic fraction was dried over Na2SO4, filtered and the filtrate was concentrated to give the title compound.

1. waitAfter 1 h at rt
2. concentrationthe reaction mixture was concentrated
3. dissolutionredissolved in 10 mL of a mixture of acetic acid and H2O (2:1)
4. stirringAfter stirring for 3 h
5. concentrationthe reaction mixture was concentrated
6. dissolutionredissolved in 100 mL of ethyl acetate
7. washThe solution was washed with sat'd NaHCO3 solution
8. dry with materialthe organic fraction was dried over Na2SO4
9. filtrationfiltered
10. concentrationthe filtrate was concentrated

ORD record

ord-1efa7193d3c64140a78632068236a87d

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06303593B1