Hydrochloric Acid → HCID 178515445, compound

HRID 594045Notes

Reaction equation

HRID 594045 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4](Cl)[CH:3]=1.Cl.[O:11]1CCOCC1>[OH-].[Na+]>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([OH:11])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 202807664-Bromo-2,6-dichloropyridine

Product 1

HCID 178515445HCID 178515445, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4-bromo-2,6-dichloropyridine (1.0 equiv.) in dioxane and aqueous sodium hydroxide (15% by weight solution, 1:1 ratio, 0.55 M) was heated in the microwave for 30 min at 150° C. The solution was cooled to room temperature and neutralized with concentrated HCl (pH=˜6) and extracted with ethyl acetate three times. The organic phase was dried with sodium sulfate, filtered and concentrated. The crude material was dried under vacuo to give 4-bromo-6-chloropyridin-2-ol as an off-white solid in 76% yield. LCMS (m/z) (M+H)=207.9/209.9, Rt=0.60 min.

Workup

  1. extractionextracted with ethyl acetate three times
  2. dry with materialThe organic phase was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dry with materialThe crude material was dried under vacuo

Sources & evidence

ORD record
ord-222f807389dc42f79e1badf4cf1dff3f
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

Loading…