Acetone → HCID 21989327, compound

HRID 1751381Notes

Reaction equation

HRID 1751381 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)[CH2:5][C:4]=2[CH:3]=1.[OH-].[K+].[CH3:18][C:19]([CH3:21])=O>C(OCC)(=O)C>[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:5](=[C:19]([CH3:21])[CH3:18])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 14797Potassium HydroxideHCID 1400732,7-Dibromofluorene

Product 1

HCID 21989327HCID 21989327, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of solid 2,7-dibromo-9H-fluorene (1 g, 3.1 mmol) and solid potassium hydroxide (freshly ground, 530 mg, 9.4 mmol) was added acetone (15 mL). The reaction immediately turns dark. After 3 hours the reaction was diluted with ethyl acetate. The organics were washed with water and brine, dried (MgSO4) and concentrated to a dark blue-green oil. This oil was dissolved in dichloromethane (10 mL) and formic acid (˜10 drops) was added until the solution was bright orange. After concentration, the resulting residue was purified by flash column chromatography to yield 2,7-dibromo-9-(propan-2-ylidene)-9H-fluorene (145 mg, 13%) as an orange solid.

Workup

  1. customThe reaction immediately turns dark
  2. washThe organics were washed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to a dark blue-green oil
  5. dissolutionThis oil was dissolved in dichloromethane (10 mL)
  6. additionformic acid (˜10 drops) was added until the solution
  7. concentrationAfter concentration
  8. customthe resulting residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-bdbdaca2334246e98b188df01a3724eb
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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