Iodine → 2-Bromo-7-iodo-9H-fluorene

HRID 1581870Notes

Reaction equation

HRID 1581870 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.S(=O)(=O)(O)O.II.[I:22](O)(=O)=O>O.C(O)(=O)C>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([I:22])=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 143362-Bromo-9H-fluoreneHCID 24345Iodic acid

Product 1

HCID 142909822-Bromo-7-iodo-9H-fluoreneYield 317%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2-bromofluorene (12.61 g, 50 mmol), acetic acid (125 mL), water (9 mL), concentrated sulfuric acid (4 mL), iodine (5.1 g, 20.1 mmol) and iodic acid (2.2 g, 12.5 mmol) was heated at 80-90° C. for 2 hours, cooled and filtered. The solids were washed with acetic acid (100 mL) and water (500 mL), to get the product 14.7 g (79% yield), m.p. 179-185° C. Mass Spec. (m/z): 418 (M+ diiodo), 370, 372 (M+iodobromo), 322, 324, 326 (M+ dibromo).

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. washThe solids were washed with acetic acid (100 mL) and water (500 mL)

Sources & evidence

ORD record
ord-ab7d9b625eb6423f9f15f925eddfbb72
Source dataset
uspto-grants-2004_05
Patent number
US06730793B1

Reaction notes

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