Potassium Iodide → 2-Bromo-9,9-didecyl-7-iodo-9H-fluorene

HRID 1268490Notes

Reaction equation

HRID 1268490 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([I:15])=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[I-].[K+].[OH-].[K+].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>CS(C)=O>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([I:15])=[CH:9][CH:10]=3)[C:5]([CH2:13][CH2:14][CH2:2][CH2:3][CH2:4][CH2:12][CH2:11][CH2:10][CH2:9][CH3:8])([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 81731-BromodecaneHCID 14797Potassium HydroxideHCID 142909822-Bromo-7-iodo-9H-fluorene

Product 1

HCID 227234762-Bromo-9,9-didecyl-7-iodo-9H-fluoreneYield 81%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mechanically stirred mixture of 7-iodo-2-bromofluorene (from example 2; 41.34 g, 0.1114 mol), DMSO (100 mL), potassium iodide (1.7 g), and powdered potassium hydroxide (28 g) cooled in a cold water bath, 1-bromodecane (53 mL) was added dropwise, and the mixture was stirred for 24 hours. The oil that separated on dilution with water, was extracted with toluene. Toluene extract was washed with water, dried and concentrated. The residual oil was passed through a column of 300 g alumina. Elution with 900 mL hexanes gave the product as an oil, 65 g This was left in 200 mL of isopropanol, when the product solidified, 58.63 g (81% yield), m.p. 43-45° C. Mass Spec.: m/z 698 (M+ diiodo), 650,652 (M+).

Workup

  1. temperaturecooled in a cold water bath
  2. customThe oil that separated on dilution with water
  3. extractionwas extracted with toluene
  4. extractionToluene extract
  5. washwas washed with water
  6. customdried
  7. concentrationconcentrated
  8. washElution with 900 mL hexanes

Sources & evidence

ORD record
ord-178d6ef90add488a88928bd178ac3426
Source dataset
uspto-grants-2003_04
Patent number
US06555682B1

Reaction notes

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