Iodine → 1,2,3-Trifluoro-4-iodobenzene

HRID 1764998Notes

Reaction equation

HRID 1764998 reaction equation
C([Li])CCC.[I:6]I.S([O-])([O-])(=O)=S.[Na+].[Na+].[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:17]=1[F:23]>C1COCC1>[I:6][C:19]1[CH:20]=[CH:21][C:16]([F:15])=[C:17]([F:23])[C:18]=1[F:22]

Participants

6

Reactant 4

HCID 807IodineHCID 151471,2,3-TrifluorobenzeneHCID 24477Sodium ThiosulfateHCID 178418339Butyllithium

Product 1

HCID 27792531,2,3-Trifluoro-4-iodobenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-60 °C

Procedure

In a nitrogen atmosphere, 1,2,3-trifluorobenzene was dissolved into THF, and cooled to −60° C. Then, butyllithium (1.56 M hexane solution) was added dropwise for 30 minutes, and stirred for 2 hours. Then, the THF solution containing iodine was added dropwise for 1 hour, and warmed to room temperature. After the reaction solution was poured into a sodium thiosulfate aqueous solution and stirred for a while, an organic layer was separated, and an aqueous layer was extracted with toluene. After the extract and the organic layer were mixed together, washed using water and a saturated saline solution in that order, and dried using anhydrous sodium sulfate, the solvent was evaporated under a reduced pressure to obtain 4-iodo-1,2,3-trifluorobenzene.

Workup

  1. additionwas added dropwise for 1 hour
  2. temperaturewarmed to room temperature
  3. stirringstirred for a while
  4. customan organic layer was separated
  5. extractionan aqueous layer was extracted with toluene
  6. extractionAfter the extract
  7. additionthe organic layer were mixed together
  8. washwashed
  9. customa saturated saline solution in that order, and dried
  10. customthe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-5ebf7efa5d394dd58cd97b60328c9223
Source dataset
uspto-grants-2007_06
Patent number
US07226644B2

Reaction notes

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