Potassium Carbonate → 4-((6-Chloropyridin-3-yl)oxy)-3-fluorobenzaldehyde

HRID 2171342Notes

Reaction equation

HRID 2171342 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[CH:5]=[O:6].[Cl:11][C:12]1[N:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[Cl:11][C:12]1[N:17]=[CH:16][C:15]([O:18][C:9]2[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=2[F:1])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5880883,4-DifluorobenzaldehydeHCID 8198212-Chloro-5-hydroxypyridine

Product 1

HCID 867241924-((6-Chloropyridin-3-yl)oxy)-3-fluorobenzaldehydeYield 78.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3,4-difluorobenzaldehyde (2.00 g, 14.8 mmol), 6-chloropyridin-3-ol (1.82 g, 14.1 mmol) and potassium carbonate (2.14 g, 15.5 mmol) in N,N-dimethylformamide (DMF) (25 mL) was stirred at 110° C. for 12 h, diluted with ethyl acetate (50 mL), washed with water (50 mL×2). The organic part was separated, dried over anhydrous Na2SO4, filtered and concentrated. Purification via silica gel (3% ethyl acetate in petroleum ether) afforded the title product (2.8 g)

Workup

  1. washwashed with water (50 mL×2)
  2. customThe organic part was separated
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification via silica gel (3% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-d00e5dc1eaa6476f8b69141d3ce99e87
Source dataset
uspto-grants-2015_06
Patent number
US09051325B2

Reaction notes

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