Iodine → 5,7-Dichloro-3-iodo-2-methylbenzofuran

HRID 1677659Notes

Reaction equation

HRID 1677659 reaction equation
[I:1]I.[Cl:3][C:4]1[CH:5]=[C:6]([Cl:14])[C:7]2[O:11][C:10]([CH3:12])=[CH:9][C:8]=2[CH:13]=1.[N+]([O-])([O-])=O.[Na+]>C(O)(=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([Cl:14])[C:7]2[O:11][C:10]([CH3:12])=[C:9]([I:1])[C:8]=2[CH:13]=1

Participants

5

Reactant 3

HCID 807IodineHCID 24268Sodium Nitrate2×HCID 608298Benzofuran, 5,7-dichloro-2-methyl-

Product 1

HCID 669337555,7-Dichloro-3-iodo-2-methylbenzofuran

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
85 °C

Procedure

A suspension of 1.7 mmol of pulverized iodine in 10 ml of glacial acetic acid is admixed with 3 mmol of 5,7-dichloro-2-methylbenzofuran [42969-57] and with 0.3 mmol of sodium nitrate. The mixture is stirred at 85° C. for 6 hours. If necessary further sodium nitrate is added after 1 hour. The reaction mixture is cooled to room temperature and quenched with 10% sodium hydrogen sulphite solution, and tert-butyl methyl ether is added. The phases are separated and the aqueous phase is extracted with tert-butyl methyl ether (3×). The combined organic phases are washed with brine, dried with sodium sulphate and evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60F) on the basis of the Rf value.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customquenched with 10% sodium hydrogen sulphite solution, and tert-butyl methyl ether
  3. additionis added
  4. customThe phases are separated
  5. extractionthe aqueous phase is extracted with tert-butyl methyl ether (3×)
  6. washThe combined organic phases are washed with brine
  7. dry with materialdried with sodium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-35202736a6c6402aa6efbae6a8177b62
Source dataset
uspto-grants-2011_08
Patent number
US08008334B2

Reaction notes

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