N-bromobutanimide → HCID 86670966, compound

HRID 515333Notes

Reaction equation

HRID 515333 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]([F:25])([F:24])[C:11]([C:17]1[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=1)([OH:16])[C:12]([F:15])([F:14])[F:13]>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:1][CH2:23][C:19]1[CH:18]=[C:17]([C:11]([OH:16])([C:12]([F:14])([F:13])[F:15])[C:10]([F:24])([F:25])[F:9])[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 10934146HCID 10934146, compound

Product 1

HCID 86670966HCID 86670966, compoundYield 21.4%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (207 mg, 1.162 mmol) was added to a solution of 1,1,1,3,3,3-hexafluoro-2-m-tolylpropan-2-ol (300 mg, 1.162 mmol) and 2,2′-azobis(isobutyronitrile) (0.191 mg, 1.162 μmol) in carbon tetrachloride (6 mL). The mixture was refluxed for 18 hours and then concentrated under reduced pressure. The crude material was dissolved in diethyl ether and heptane, filtered through dicalite, and purified by silica chromatography (eluting with a solvent gradient from 2% ethyl acetate/98% heptane to 10% ethyl acetate/90% heptane) to afford the title compound (84 mg).

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe crude material was dissolved in diethyl ether
  4. filtrationheptane, filtered through dicalite
  5. custompurified by silica chromatography (
  6. washeluting with a solvent gradient from 2% ethyl acetate/98% heptane to 10% ethyl acetate/90% heptane)

Sources & evidence

ORD record
ord-1604c08766284abebeda5a9a50c30d68
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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