Hydrogen Peroxide → HCID 58042375, compound

HRID 2048114Notes

Reaction equation

HRID 2048114 reaction equation
[OH:1]O.[F:3][C:4]([F:29])([CH:26]([F:28])[F:27])[CH2:5][O:6][C:7]1[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10](B2OC(C)(C)C(C)(C)O2)=[CH:9][N:8]=1>CO>[F:3][C:4]([F:29])([CH:26]([F:28])[F:27])[CH2:5][O:6][C:7]1[N:8]=[CH:9][C:10]([OH:1])=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 58042473HCID 58042473, compound

Product 1

HCID 58042375HCID 58042375, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrogen peroxide (1.29 mL, 13.33 mmol, 35% solution) was added to a solution of 2-(2,2,3,3-tetrafluoropropoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridine (Preparation 261, 4.45 g, 11.04 mmol) in methanol (50 mL) at 0° C. (ice-bath) and the reaction mixture was allowed to warm to room temperature. After 3 hours, the reaction was quenched with 1M solution of sodium thiosulfate and then methanol was removed in vacuo. The residue was partitioned between ethyl acetate and water, the organic layer was dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated in vacuo. The crude product was purified by flash chromatography on silica gel eluting with 30% heptane in ethyl acetate to give the title compound as a oil (2.95 g, 91%).

Workup

  1. customthe reaction was quenched with 1M solution of sodium thiosulfate
  2. custommethanol was removed in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe crude product was purified by flash chromatography on silica gel eluting with 30% heptane in ethyl acetate

Sources & evidence

ORD record
ord-3eafdac8b90d4223a341aee0d1682e2b
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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