Hydrogen Peroxide → 2,6-Dichloropyridin-3-ol

HRID 1776792Notes

Reaction equation

HRID 1776792 reaction equation
[OH:1]O.[Cl:3][C:4]1[C:9](B(O)O)=[CH:8][CH:7]=[C:6]([Cl:13])[N:5]=1>C(Cl)Cl>[Cl:3][C:4]1[C:9]([OH:1])=[CH:8][CH:7]=[C:6]([Cl:13])[N:5]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 27627122,6-Dichloropyridine-3-boronic acid

Product 1

HCID 1043172,6-Dichloropyridin-3-olYield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

H2O2 (1.60 g, 47.12 mmol) was added slowly to the solution of compound 2,6-dichloropyridin-3-ylboronic acid (3 g, 15.71 mmol) in CH2Cl2 (30 mL) at 0° C. After stirred at room temperature for about 15 hours, the mixture was quenched with sat. Na2S2O3 aqueous (50 mL) and adjusted to pH<7 with 1N HCl. The mixture was extracted with EtOAc (40 mL×3). The organic layer was washed with brine (100 mL), dried over Na2SO4, filtered and the solvent was concentrated in vacuo to provide 2,6-dichloropyridin-3-ol (2.34 g, yield: 91.4%). 1H-NMR (CDCl3, 400 MHz) δ 7.30 (d, J=8.4 Hz, 1H), 7.19 (d, J=8.4 Hz, 1H), 5.70 (br, 1H). MS (M+H)+: 164/166/168.

Workup

  1. customthe mixture was quenched with sat. Na2S2O3 aqueous (50 mL)
  2. extractionThe mixture was extracted with EtOAc (40 mL×3)
  3. washThe organic layer was washed with brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-31785d038d904b1ca092b5e430f1d88e
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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