Water → 6-(4-Fluorophenoxy)pyridin-3-ol

HRID 533895Notes

Reaction equation

HRID 533895 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CC(OC)(C)C>[F:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:2]2[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 97324-FluorophenolHCID 10796Cesium carbonateHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 590890276-(4-Fluorophenoxy)pyridin-3-ol

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 6-bromo-pyridin-3-ol (8.0 g), 4-fluorophenol (15.5 g) and cesium carbonate (30 g) was heated to 170° C. for 6 hours. After the mixture reached room temperature, it was distributed between water and MTBE. The organic phase was dried (Na2SO4) and concentrated. The residue was purified by chromatography (SiO2; EA/heptane 1:1.5) to provide the subtitle compound. MS ESI+: m/z=206 [M+H]+.

Workup

  1. customreached room temperature
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography (SiO2; EA/heptane 1:1.5)

Sources & evidence

ORD record
ord-68a0ea0c070d4f91adbacd02ef8446ae
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Reaction notes

Loading…