Cesium carbonate → 2,3-Dichloro-5-(2-methoxyethoxy)pyridine

HRID 81664Notes

Reaction equation

HRID 81664 reaction equation
[CH3:1][O:2][CH2:3][CH2:4]Br.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:12][C:13]1[CH:14]=[C:15]([OH:20])[CH:16]=[N:17][C:18]=1[Cl:19].O.[Cl-].[NH4+]>C(OCC)(=O)C.CN(C)C(=O)C>[Cl:19][C:18]1[C:13]([Cl:12])=[CH:14][C:15]([O:20][CH2:4][CH2:3][O:2][CH3:1])=[CH:16][N:17]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 143916722,3-Dichloro-5-hydroxypyridineHCID 57429219Ammonium chloride monohydrate

Product 1

HCID 866459022,3-Dichloro-5-(2-methoxyethoxy)pyridineYield 85%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromoethyl methyl ether (0.44 ml, 4.57 mmol) and cesium carbonate (2.48 g, 7.62 mmol) were added to an N,N-dimethylacetamide solution (5 ml) of 5,6-dichloropyridin-3-ol (500 mg, 3.05 mmol), and stirred under a nitrogen atmosphere at 80° C. for 5 hours. The reaction solution was cooled with ice, then ammonium chloride water and ethyl acetate were added, the organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Biotage, hexane:ethyl acetate=9:1) to obtain 2,3-dichloro-5-(2-methoxyethoxy)pyridine (573 mg, yield: 85%) as an orange oil.

Workup

  1. temperatureThe reaction solution was cooled with ice
  2. washthe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (Biotage, hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-32deaa2d4ebe4137b2c57faecb2d6491
Source dataset
uspto-grants-2014_09
Patent number
US08846700B2

Reaction notes

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