Iodine → 2-Bromo-8-iododibenzofuran

HRID 1669919

Reaction equation

HRID 1669919 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]2[O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[I:15](O)(O)(O)(O)(O)=O.II.S(=O)(=O)(O)O>O.C(O)(=O)C>[Br:1][C:2]1[CH:14]=[CH:13][C:5]2[O:6][C:7]3[CH:12]=[CH:11][C:10]([I:15])=[CH:9][C:8]=3[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 68562-BromodibenzofuranHCID 25289Orthoperiodic acid

Product 1

HCID 673359322-Bromo-8-iododibenzofuran

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

2-Bromodibenzofuran (2.5 g, 10.1 mmol), orthoperiodic acid (0.49 g, 2.15 mmol), iodine (1.02 g, 4.02 mmol), sulfuric acid, H2O (2 ml) and acetic acid (10 ml) are put into a reaction vessel and the mixture is stirred at 70° C. for 3 hours. After cooling to room temperature the reaction mixture is poured into water and filtered. The white solid is washed by methanol and the desired product is obtained (1.92 g, 51%).

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. filtrationfiltered
  3. washThe white solid is washed by methanol

Sources & evidence

ORD record
ord-9852295a50264bfe8ffa77266eda349a
Source dataset
uspto-grants-2011_08
Patent number
US07989644B2

Linked notes

Loading…