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Water → 9,9-Dibutyl-2-nitro-9H-fluorene

HRID 630643
Notes
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Reaction equation

HRID 630643 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1)([O-:3])=[O:2].[OH-].[K+].[I-].[K+].O>CS(C)=O>[CH2:16]([C:7]1([CH2:7][CH2:8][CH2:9][CH3:10])[C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:4][CH2:5][CH3:6]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 118312-NitrofluoreneHCID 14797Potassium Hydroxide

Product 1

HCID 444715309,9-Dibutyl-2-nitro-9H-fluoreneYield 158.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl Sulfoxide
Solvent

Conditions

Temperature
15 °C

Procedure

12.66 g of 2-nitrofluorene (1) (60 mmol), 21.0 g of potassium hydroxide (0.3 mol, purity: 80%), and 1.01 g of potassium iodide (6 mmol) were dissolved in 200 ml of anhydrous dimethylsulfoxide under nitrogen atmosphere, and a reaction temperature was maintained at 15° C. Then, 33 ml of n-bromobutane (0.3 mol) was slowly added thereto for 2 hours, followed by stirring at 15° C. for 1 hour. Thereafter, 200 ml of distilled water was added to the reaction mixture and stirred for about 30 minutes, a product was extracted with 300 ml of dichloromethane, and the extracted organic layer was washed with 100 ml of distilled water three times. Then, the recovered organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled under reduced pressure. The obtained product was purified using a silica gel column chromatography (eluent: dichloromethane:n-hexane=20:1), thereby obtaining 15.4 g of 9,9-di-n-butyl-2-nitrofluorene (5) (79.5%) as a light yellow product.

Workup

  1. stirringstirred for about 30 minutes
  2. extractiona product was extracted with 300 ml of dichloromethane
  3. washthe extracted organic layer was washed with 100 ml of distilled water three times
  4. dry with materialThen, the recovered organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled under reduced pressure
  6. customThe obtained product was purified

Sources & evidence

ORD record
ord-146d8a8000824b8cb558b0638bf11f17
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09316906B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes