Hydrochloric Acid → (6-Fluoropyridin-3-yl)boronic acid

HRID 1913356Notes

Reaction equation

HRID 1913356 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:8])=[N:6][CH:7]=1.[Li]CCCC.[B:14](OC(C)C)([O:19]C(C)C)[O:15]C(C)C.Cl>>[B:14]([OH:19])([OH:15])[C:2]1[CH:3]=[CH:4][C:5]([F:8])=[N:6][CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 27831685-Bromo-2-fluoropyridineHCID 178418339Butyllithium

Product 1

HCID 2783397(6-Fluoropyridin-3-yl)boronic acidYield 74%

Procedure

5-Bromo-2-fluoropyridine was treated with n-BuLi (1.6 M in hexanes, 19.5 mL, 31.3 mmol), triisopropyl borate (7.9 mL, 34.1 mmol) and HCl(aq) (2.7 N, 28.4 mL) as for 1 to give the title compound 2 (3.0 g, 74% yield) as a brown semi-solid: 1H NMR (CD3OD) δ 8.45 (br s, 1H), 8.21 (br s, 1H), 7.01 (m, 1H). This material was used directly in Suzuki cross coupling reactions.

Sources & evidence

ORD record
ord-6422c113768245d5ba1b6ad5f182dc44
Source dataset
uspto-grants-2013_12
Patent number
US08609708B2

Reaction notes

Loading…