Iodine → HCID 178448027, compound

HRID 1764994Notes

Reaction equation

HRID 1764994 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[C@H:10]1[CH2:15][CH2:14][C@H:13]([C@H:16]2[CH2:21][CH2:20][C@H:19]([CH2:22][CH2:23][CH3:24])[CH2:18][CH2:17]2)[CH2:12][CH2:11]1.C([Li])CCC.[I:30]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1COCC1>[I:30][C:5]1[C:6]([F:9])=[C:7]([F:8])[C:2]([F:1])=[C:3]([C@H:10]2[CH2:11][CH2:12][C@H:13]([C@H:16]3[CH2:21][CH2:20][C@H:19]([CH2:22][CH2:23][CH3:24])[CH2:18][CH2:17]3)[CH2:14][CH2:15]2)[CH:4]=1

Participants

6

Reactant 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 178418339ButyllithiumHCID 178448018HCID 178448018, compound

Product 1

HCID 178448027HCID 178448027, compoundYield 107.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-60 °C

Procedure

In a nitrogen atmosphere, 17 g of 2,3,4-trifluoro-1-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]benzene was dissolved into 300 mL of THF, and cooled to −60° C. Into this, 39 mL of butyllithium (1.56 M of hexane solution) was added dropwise for 30 minutes, and stirred for 2 hours. Into this, a THF solution (50 mL) containing 14 g of 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 magnesium sulfate, the solvent was evaporated under a reduced pressure to obtain 25 g of 5-iodo-2,3,4-trifluoro-1-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]benzene.

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-5f3103b453f14cb59f00810e5e257999
Source dataset
uspto-grants-2007_06
Patent number
US07226644B2

Reaction notes

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