Iodine → 2-Bromo-7-iodo-9H-fluorene

HRID 1268489Notes

Reaction equation

HRID 1268489 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 yield 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-cd2ac7e24ed2433eb8ebef90ae186ca0
Source dataset
uspto-grants-2003_04
Patent number
US06555682B1

Reaction notes

Loading…