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

HRID 1895759Notes

Reaction equation

HRID 1895759 reaction equation
C[C:2]([CH3:5])([O-])[CH3:3].[K+].[Br:7][C:8]1[CH:20]=[CH:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][C:10]=2[CH:9]=1.[CH2:21](I)[CH2:22][CH2:23][CH3:24].[CH3:26]S(C)=O>C(Cl)(Cl)Cl>[Br:7][C:8]1[CH:20]=[CH:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([CH2:26][CH2:3][CH2:2][CH3:5])([CH2:21][CH2:22][CH2:23][CH3:24])[C:10]=2[CH:9]=1

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 10962Butyl iodideHCID 143362-Bromo-9H-fluoreneHCID 23665647Potassium tert-butoxide

Product 1

HCID 223816472-Bromo-9,9-dibutyl-9H-fluorene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Under a nitrogen atmosphere, to a solution obtained by dissolving 20.8 parts of potassium tert-butoxide in 102 parts of dimethylsulfoxide (DMSO), a solution obtained by dissolving 15.4 parts of 2-bromofluorene in 153 parts of dimethylsulfoxide (DMSO) was added dropwise. After stirring for 30 minutes, while keeping the reaction solution temperature to 40 to 45° C., 27.8 parts of butyl iodide was added dropwise. After stirring at 40° C. for 40 minutes, the reaction solution was added to ice water. The reaction mixture was extracted with chloroform-water, the chloroform phase was dried over magnesium sulfate, and then chloroform was distilled off to obtain a brown tarry solid. This brown tarry solid was dissolved in a small amount of chloroform, and separated and purified by column chromatography (hexane) to obtain 12.6 parts of 2-bromo-9,9-dibutylfluorene as a colorless crystal.

Workup

  1. customUnder a nitrogen atmosphere, to a solution obtained
  2. customa solution obtained
  3. additionwas added dropwise
  4. customto 40 to 45° C.
  5. stirringAfter stirring at 40° C. for 40 minutes
  6. extractionThe reaction mixture was extracted with chloroform-water
  7. dry with materialthe chloroform phase was dried over magnesium sulfate
  8. distillationchloroform was distilled off
  9. customto obtain a brown tarry solid
  10. customseparated
  11. custompurified by column chromatography (hexane)

Sources & evidence

ORD record
ord-b8daf464d43342508dd127168c6cac59
Source dataset
uspto-grants-2013_08
Patent number
US08513520B2

Reaction notes

Loading…