Hydrochloric Acid → 2-Cyano-phenylboric acid

Temperature

-76 °C

12.4 ml of a 1.6 M solution of t-butyllithium in n-pentane was dropwise added to 23 ml of THF at −76° C. in about 10 minutes. Then, a solution of 2.0 g (11.0 mmo ) of 2-bromobenzonitrile in 3.0 ml. of THF was dropwise added to the resulting mixture at −76° C. in about 20 minutes, followed by the dropwise addition of 2.3 ml (19.8 mmol) of trimethoxyborane in 7 minutes. The obtained mixture was stirred at −76° C. for 20 minutes, followed by the addition of 13.8 ml of 2N hydrochloric acid. The obtained mixture was stirred at room temperature for 30 minutes and extracted with ethyl acetate. The ethyl acetate phase was washed with water and a saturated brine, dried and distilled to remove the solvent. 15 ml of methylene chloride and 15 ml of n-hexane were added to the obtained residue. The obtained mixture was stirred at room temperature for 30 minutes to give a precipitate. The precipitate was recovered by filtration and dried to give 0.9 g of the title compound (yield: 55.7%).

1. stirringThe obtained mixture was stirred at room temperature for 30 minutes
2. extractionextracted with ethyl acetate
3. washThe ethyl acetate phase was washed with water
4. dry with materiala saturated brine, dried
5. distillationdistilled
6. customto remove the solvent
7. addition15 ml of methylene chloride and 15 ml of n-hexane were added to the obtained residue
8. stirringThe obtained mixture was stirred at room temperature for 30 minutes
9. customto give a precipitate
10. filtrationThe precipitate was recovered by filtration
11. customdried

ORD record

ord-44b71ad8881b4693a285acf43cbc0a64

Source dataset

uspto-grants-2001_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06281214B1