Potassium Carbonate → 3,5-Difluoro-4-((6-(trifluoromethyl)-3-pyridinyl)oxy)benzaldehyde

HRID 920285Notes

Reaction equation

HRID 920285 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1F)[CH:5]=[O:6].[F:12][C:13]([F:22])([F:21])[C:14]1[N:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[F:11][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([F:1])[C:9]=1[O:20][C:17]1[CH:18]=[N:19][C:14]([C:13]([F:22])([F:12])[F:21])=[CH:15][CH:16]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27769543,4,5-TrifluorobenzaldehydeHCID 27833885-Hydroxy-2-(trifluoromethyl)pyridine

Product 1

HCID 866763653,5-Difluoro-4-((6-(trifluoromethyl)-3-pyridinyl)oxy)benzaldehydeYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

3,4,5-trifluorobenzaldehyde (1 g, 6.25 mmol), which is commercially available 6-(trifluoromethyl)-3-pyridinol (1.019 g, 6.25 mmol) and K2CO3 (1.727 g, 12.49 mmol) were added into a microwave vial. Then, N,N-dimethylformamide (DMF) (15 mL) was added. The microwave vial was sealed and heated in Biotage Initiator at 100° C. for 1 h. The mixture was extracted with by EtOAc. The organic extracts were dried over Na2SO4 and evaporated to give 1.78 g of the title product (94%).

Workup

  1. additionwere added into a microwave vial
  2. customThe microwave vial was sealed
  3. extractionThe mixture was extracted with by EtOAc
  4. dry with materialThe organic extracts were dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-a3db273e9c88422893768e48912f1c52
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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