p-Fluoronitrobenzene → 1-(2,2,3,3,4,4,4-Heptafluorobutoxy)-4-nitrobenzene

HRID 630320Notes

Reaction equation

HRID 630320 reaction equation
[F:1][C:2]([F:12])([C:5]([F:11])([F:10])[C:6]([F:9])([F:8])[F:7])[CH2:3][OH:4].[H-].[Na+].F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1>CN(C=O)C>[F:1][C:2]([F:12])([C:5]([F:10])([F:11])[C:6]([F:7])([F:8])[F:9])[CH2:3][O:4][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 9776HeptafluorobutanolHCID 24758Sodium hydride

Product 1

HCID 178288771-(2,2,3,3,4,4,4-Heptafluorobutoxy)-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,2,3,3,4,4,4-heptafluorobutanol (5.7 g, 28.5 mmol) in DMF (100 mL) was stirred and cooled to −5° C. as sodium hydride (0.72 g, 30 mmol) was added. After 1 h at −5° C., the reaction was treated with 4-fluoronitrobenzene (4.1 g, 29 mmol). The reaction was allowed to warm to ambient temperature, concentrated, and slurried in methylene chloride (200 mL). The slurry was washed with an 1 N aqueous potassium hydroxide solution (2×) and brine solution, dried over basic alumina, treated with charcoal, filtered, and concentrated to give 4-(2′,2′,3′,3′,4′,4′,4′-heptafluorobutanoxy)nitrobenzene.

Workup

  1. additionwas added
  2. concentrationconcentrated
  3. washThe slurry was washed with an 1 N aqueous potassium hydroxide solution (2×) and brine solution
  4. customdried over basic alumina
  5. additiontreated with charcoal
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-62eae897f7904a0d93674d4af17a9095
Source dataset
uspto-grants-2016_04
Patent number
US09315509B2

Reaction notes

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