Iodine → 4-Ethyl-4'-iodobiphenyl

HRID 1860356

Reaction equation

HRID 1860356 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)[CH3:2].[I:15](O)(O)(O)(O)(O)=O.II.S(=O)(=O)(O)O>O.C(O)(=O)C>[I:15][C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 25289Orthoperiodic acidHCID 797864-Ethylbiphenyl

Product 1

HCID 154778284-Ethyl-4'-iodobiphenyl

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

25.0 g (137 mmol) of 4-ethylbiphenyl, 7.23 g (27.4 mmol) of orthoperiodic acid, 13.9 g (54.9 mmol) of iodine, 133 ml of acetic acid, 27 ml of water and 4.1 ml of sulfuric acid were placed in a 500 ml three-necked flask with a mechanical stirrer and bulb-shaped cooler. This was heated to 70° C. in a water bath, and subjected to the reaction for 2 hours. The product was cooled down to the ambient temperature. To this was added 300 ml of water, which was subjected to the extraction with chloroform. The resultant chloroform phase was washed with sodium thiosulfate and water in this order. To this was added sodium sulfate, and the dehydration was carried out. After the filtration was carried out, the chloroform was distilled away in an evaporator to obtain a light yellow solid. The resultant solid was recrystallized in the presence of ethanol to obtain a white crystal. The yield of the compound was 71%. Its melting point was 145-149° C. The IR chart is shown in FIG. 24.

Workup

  1. customsubjected to the reaction for 2 hours
  2. temperatureThe product was cooled down to the ambient temperature
  3. extractionwas subjected to the extraction with chloroform
  4. washThe resultant chloroform phase was washed with sodium thiosulfate and water in this order
  5. additionTo this was added sodium sulfate
  6. filtrationAfter the filtration
  7. distillationthe chloroform was distilled away in an evaporator
  8. customto obtain a light yellow solid
  9. customThe resultant solid was recrystallized in the presence of ethanol
  10. customto obtain a white crystal

Sources & evidence

ORD record
ord-5e84395f5d5244698bb30c6892a000d9
Source dataset
uspto-grants-2003_03
Patent number
US06528657B2

Linked notes

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