Potassium Carbonate → HCID 68510351, compound

HRID 1952347Notes

Reaction equation

HRID 1952347 reaction equation
[Cl:1][C:2]1[C:3]([F:11])=[N:4][C:5]([F:10])=[C:6]([F:9])[C:7]=1F.[Cl:12][C:13]1[CH:14]=[C:15]([OH:21])[CH:16]=[C:17]([C:19]#[N:20])[CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:12][C:13]1[CH:18]=[C:17]([CH:16]=[C:15]([O:21][C:7]2[C:6]([F:9])=[C:5]([F:10])[N:4]=[C:3]([F:11])[C:2]=2[Cl:1])[CH:14]=1)[C:19]#[N:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1371833-Chloro-2,4,5,6-tetrafluoropyridineHCID 219498783-Chloro-5-hydroxybenzonitrile

Product 1

HCID 68510351HCID 68510351, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-50 °C

Procedure

3-Chloro-2,4,5,6-tetrafluoropyridine (10-1; 1.0 g; 5.39 mmol) and Compound 1-4 (0.83 g; 5.39 mmol) were dissolved in DMF and the solution cooled to −50° C. under a nitrogen atmosphere, after which potassium carbonate (1.12 g; 8.09 mmol) was added and the mixture allowed to slowly warm to 25° C. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic extract was concentrated and purified on a silica column eluted with ethyl acetate:hexane to give the title product 10-2 as a clear oil. Rf=0.6 (EtOAc:hx, 5:95). 1H NMR (CDCl3): δ 7.50 (s, 1H), 7.24 (s, 1H), 7.17 (s, 1H).

Workup

  1. temperatureto slowly warm to 25° C
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. concentrationwas concentrated
  6. custompurified on a silica column
  7. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-70ce0e65577044c991fbd88496b672a0
Source dataset
uspto-grants-2013_03
Patent number
US08404856B2

Reaction notes

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