Methyl iodide → 2,7-Dibromo-9,9-dimethylfluorene

HRID 1185812Notes

Reaction equation

HRID 1185812 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)C[C:4]=2[CH:3]=1.[OH-].[K+].[CH3:18]I.C(O[CH2:24][CH3:25])(=O)C>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:24]([CH3:25])([CH3:18])[C:13]=2[CH:14]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 1400732,7-Dibromofluorene

Product 1

HCID 121238762,7-Dibromo-9,9-dimethylfluoreneYield 100%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 2,7-dibromo-9H-fluorene (1.0 g, 3.1 mmol), KI (50 mg, 0.3 mmol) and KOH (750 mg, 13.3 mmol) in DMSO was added methyl iodide (0.42 mL, 6.8 mmol). The mixture was stirred at room temperature for 16 hours, then diluted with ethyl acetate (100 mL). The organic layer was washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide the desired product 2,7-Dibromo-9,9-dimethyl-9H-fluorene as a white solid (1.1 g, 100%).

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified by flash chromatography

Sources & evidence

ORD record
ord-075815b63ee64c80827c2e642edae805
Source dataset
uspto-grants-2014_03
Patent number
US08669234B2

Reaction notes

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