p-Fluoronitrobenzene → HCID 53399663, compound

HRID 2362267Notes

Reaction equation

HRID 2362267 reaction equation
CC(C)([O-])C.[K+].[CH3:7][N:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]1.F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1>C1COCC1>[CH3:7][N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[CH2:9]1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 930741-Methyl-3-pyrrolidinolHCID 23665647Potassium tert-butoxide

Product 1

HCID 53399663HCID 53399663, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of potassium tert-butoxide (1.43 g, 12.9 mmol) in THF (6 mL) was added 1-methylpyrrolidin-3-ol (645 mg, 6.39 mmol). The reaction mixture was stirred at room temperature for 1 h. Then 1-fluoro-4-nitrobenzene (900 mg, 6.39 mmol) was added to the above solution and stirred for another 2 h. After the removal of the volatile, the residual was dissolved in ethyl acetate (40 mL), and then washed with water (20 mL) and brine (20 mL), dried over Na2SO4, filtered, concentrated and purified by silica gel column chromatography (EA:PE=1:4) to give desired product as a yellow oil (626 mg, 44%).

Workup

  1. stirringstirred for another 2 h
  2. customAfter the removal of the volatile, the residual
  3. dissolutionwas dissolved in ethyl acetate (40 mL)
  4. washwashed with water (20 mL) and brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatography (EA:PE=1:4)

Sources & evidence

ORD record
ord-24b9bc3ed4d94a95834ec196680d0a70
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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