Water → 2-Bromo-9H-fluorene

HRID 25486

Reaction equation

HRID 25486 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.O.[Br:15]Br.S([O-])(O)=O.[Na+]>S(=O)(=O)(O)O.C1(C)C=CC=CC=1>[Br:15][C:9]1[CH:8]=[CH:7][C:6]2[C:5]3[C:13](=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH2:12][C:11]=2[CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6853FluoreneHCID 24408Bromine2×HCID 23665763Sodium Bisulfite

Product 1

HCID 143362-Bromo-9H-fluoreneYield 82%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 1140TolueneSolvent

Procedure

In a three-liter flask having four openings equipped with a stirrer, a thermometer, a dropping funnel, and a reflux condenser, respectively, 237 g (1.4 mol) of fluorene, 1 L of water, three drops of a surfactant, and five drops of sulfuric acid were placed and stirred to mix. By adding 230 g (1.4 mol) of bromine into the mixture, a reaction was started. After the reaction had been conducted at room temperature for 5 hours, unreacted bromine was decomposed with an aqueous solution of sodium hydrogen sulfite. The reaction product, which was a light yellow solid, was filtered and thus 334 g of a crude product was obtained. The crude product was dissolved in toluene and was subsequently washed with water and a sodium hydrogencarbonate aqueous solution. The resulting organic liquid was dried using anhydrous magnesium sulfate. After filtration, the liquid was concentrated and then allowed to stand at 0° C., so that a white solid was precipitated. The precipitate was filtered and subsequently washed with toluene, followed by drying. Thus, 287 g (1.1 mol, yield of 82%) of a white solid product was obtained. This product was subjected to gas chromatography and the purity of the product was 98.8%.

Workup

  1. customequipped with a stirrer
  2. additionto mix
  3. filtrationwas filtered
  4. customthus 334 g of a crude product was obtained
  5. washwas subsequently washed with water
  6. customThe resulting organic liquid was dried
  7. filtrationAfter filtration
  8. concentrationthe liquid was concentrated
  9. customto stand at 0° C., so that a white solid
  10. customwas precipitated
  11. filtrationThe precipitate was filtered
  12. washsubsequently washed with toluene
  13. customby drying

Sources & evidence

ORD record
ord-0756538c8d9f4afa86698da3925b6c16
Source dataset
uspto-grants-2005_02
Patent number
US06858764B2

Linked notes

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