Potassium Carbonate → 3-Fluoro-4-((6-(trifluoromethyl)pyridin-2-yl)oxy)benzaldehyde

HRID 705918Notes

Reaction equation

HRID 705918 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[N:8]=[C:7]([OH:9])[CH:6]=[CH:5][CH:4]=1.[F:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1F)[CH:16]=[O:17].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CC(=O)OCC>[F:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:9][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([C:2]([F:1])([F:10])[F:11])[N:8]=1)[CH:16]=[O:17]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5880883,4-DifluorobenzaldehydeHCID 178516021HCID 178516021, compound

Product 1

HCID 866662133-Fluoro-4-((6-(trifluoromethyl)pyridin-2-yl)oxy)benzaldehydeYield 44.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 6-(trifluoromethyl)pyridin-2-ol (1.205 g, 7.39 mmol) in DMF (7 mL), was added 3,4-difluorobenzaldehyde (0.776 mL, 7.04 mmol) and K2CO3 (1.167 g, 8.44 mmol). The mixture was heated with a microwave condition at 150° C. for 1 h. After cooling, the mixture was diluted with EA, washed with water, brine, and concentrated. The residue was purified via flash chromatography to afford the title compound (890 mg, 44.3% yield) as a white solid. LCMS: rt=2.62 min, [M+H+]=286

Workup

  1. temperatureAfter cooling
  2. washwashed with water, brine
  3. concentrationconcentrated
  4. customThe residue was purified via flash chromatography

Sources & evidence

ORD record
ord-7dda17717725448d909b24c827937f66
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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