Hydrochloric Acid → 2-Chloropyridine-5-boronic acid

HRID 1913358Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([Cl: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]([Cl:8])=[N:6][CH:7]=1

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 21531Triisopropyl borate

HCID 27344145-Bromo-2-chloropyridine

HCID 178418339Butyllithium

Product 1

HCID 38450342-Chloropyridine-5-boronic acidYield 60%

Procedure

5-Bromo-2-chloropyridine was treated with n-BuLi (1.6 M in hexanes, 12.0 mL, 19.1 mmol), triisopropyl borate (4.8 mL, 20.9 mmol) and HCl(aq) (2.7 N, 16.8 mL) as for 1 to give the title compound 4 (1.7 g, 60% yield) as a pink solid: 1H NMR (CD3OD) δ 8.58 (br s, 1H), 7.95 (br d, J=6.7 Hz, 1H), 7.95 (d, J=8 Hz, 1H). This material was used directly in Suzuki cross coupling reactions.

Sources & evidence

ORD record: ord-6d70b553d1744dd7a4c43e676793d250
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609708B2

Reaction notes

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