Potassium Iodide → HCID 86682573, compound

HRID 512070Notes

Reaction equation

HRID 512070 reaction equation
[I-:1].[K+].F[B-](F)(F)F.[Cl:8][C:9]1[CH:10]=[C:11]([N+]#N)[CH:12]=[N:13][C:14]=1[O:15][CH:16]([C:21]([F:24])([F:23])[F:22])[C:17]([F:20])([F:19])[F:18]>CC(C)=O>[Cl:8][C:9]1[C:14]([O:15][CH:16]([C:21]([F:24])([F:23])[F:22])[C:17]([F:20])([F:19])[F:18])=[N:13][CH:12]=[C:11]([I:1])[CH:10]=1

Participants

4

Reactant 2

HCID 4875Potassium IodideHCID 86682571HCID 86682571, compound

Product 1

HCID 86682573HCID 86682573, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium iodide (421 mg, 2.53 mmol) was added to a solution of 5-chloro-6-(1,1,1,3,3,3-hexafluoropropan-2-yloxy)pyridine-3-diazonium tetra fluoroborate (Preparation 53, 200 mg, 0.51 mmol) in acetone (10 mL). The mixture was stirred for 15 minutes at room temperature then concentrated in vacuo. The resulting crude residue was partitioned between EtOAc and water. The aqueous layer was further extracted with EtOAc. The combined organics were dried over magnesium sulfate and concentrated in vacuo. The crude material was purified by silica gel chromatography eluting with 10% diethyl ether in heptane to afford the title compound as an orange oil.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe resulting crude residue was partitioned between EtOAc and water
  3. extractionThe aqueous layer was further extracted with EtOAc
  4. dry with materialThe combined organics were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by silica gel chromatography
  7. washeluting with 10% diethyl ether in heptane

Sources & evidence

ORD record
ord-af1fca1848d04975b7c1a352d78d1863
Source dataset
uspto-grants-2015_08
Patent number
US09102621B2

Reaction notes

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