Dimethyl Sulfoxide → 9,9-dibutyl-2-iodo-9H-fluorene

HRID 1029064

Reaction equation

HRID 1029064 reaction equation
[I:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.C[C:16]([CH3:19])([O-])[CH3:17].[K+].[CH2:21](I)[CH2:22][CH2:23][CH3:24].[CH3:26]S(C)=O>O1CCCC1>[CH2:21]([C:5]1([CH2:26][CH2:17][CH2:16][CH3:19])[C:4]2[CH:3]=[C:2]([I:1])[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10962Butyl iodide2×HCID 2240942-Iodo-9H-fluoreneHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 230728539,9-dibutyl-2-iodo-9H-fluorene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

20 parts of 2-iodofluorene was dissolved in a mixed solution of 114 parts of dimethyl sulfoxide (DMSO) and 23 parts of tetrahydrofuran (THF), and the thus obtained mixture was then stirred at 25° C. for 10 minutes. Thereafter, while stirring, 8.6 parts of potassium-tert-butoxide was added to the mixture. Twenty minutes later, 14.6 parts of butyl iodide was added to the mixture, and further twenty minutes later, 8.6 parts of potassium-tert-butoxide was added thereto. Further, twenty minutes later, 14.6 parts of butyl iodide was added thereto, and the obtained mixture was then stirred at 25° C. for 2 hours. After completion of the stirring, THF was distilled away from the reaction solution, and it was then extracted with toluene-water. The toluene phase was dried over magnesium sulfate, and toluene was then distilled away, thereby obtaining a brown tarry solid. This brown tarry solid was separated and purified by column chromatography (hexane-ethyl acetate) to obtain 25 parts of 9,9-dibutyl-2-iodofluorene in the form of a colorless crystal.

Workup

  1. stirringThereafter, while stirring
  2. stirringthe obtained mixture was then stirred at 25° C. for 2 hours
  3. distillationAfter completion of the stirring, THF was distilled away from the reaction solution, and it
  4. extractionwas then extracted with toluene-water
  5. dry with materialThe toluene phase was dried over magnesium sulfate, and toluene
  6. distillationwas then distilled away
  7. customobtaining a brown tarry solid
  8. customThis brown tarry solid was separated
  9. custompurified by column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-2f03f86e82c54fe2b75ef364dc7adb49
Source dataset
uspto-grants-2014_05
Patent number
US08735720B2

Linked notes

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