Hydrochloric Acid → [5-(Trifluoromethyl)pyridin-3-yl]boronic acid

HRID 1396582Notes

Reaction equation

HRID 1396582 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[B:12](OCC)([O:16]CC)[O:13]CC.[Li]CCCC.Cl>C1COCC1>[F:9][C:8]([F:11])([F:10])[C:6]1[CH:7]=[C:2]([B:12]([OH:16])[OH:13])[CH:3]=[N:4][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9009Triethyl borateHCID 111279913-Bromo-5-(trifluoromethyl)pyridineHCID 178418339Butyllithium

Product 1

HCID 45158900[5-(Trifluoromethyl)pyridin-3-yl]boronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A cooled (−78° C.) solution of 3-bromo-5-(trifluoromethyl)pyridine (5 g, 22.1 mmol) in dry THF (50 ml), under an inert atmosphere of argon, is treated with triethyl borate (3.39 g, 23.21 mmol) followed by drop wise addition of 1.46M n-BuLi in hexanes (15.2 ml, 24.34 mmol). The reaction mixture is allowed to warm to room temperature overnight and treated with 5M HCl (100 ml). After stirring for 30 minutes, the THF is removed in vacuo and the aqueous layer is extracted with EtOAc (4×100 ml). The aqueous portion is concentrated in vacuo and dried under vacuum overnight to afford the title compound as the hydrochloride salt. [M+H]+ 168.

Workup

  1. customthe THF is removed in vacuo
  2. extractionthe aqueous layer is extracted with EtOAc (4×100 ml)
  3. concentrationThe aqueous portion is concentrated in vacuo
  4. customdried under vacuum overnight

Sources & evidence

ORD record
ord-0c67a1bc41914b55b60db80d82df1cc8
Source dataset
uspto-grants-2014_12
Patent number
US08901134B2

Reaction notes

Loading…