Iodine → HCID 178450060, compound

HRID 2074047Notes

Reaction equation

HRID 2074047 reaction equation
S(=O)(=O)(O)O.[CH2:6]([O:10][C:11]1[CH:20]=[C:19]2[C:14]([CH:15]=[C:16]([CH2:23][CH2:24][C@H:25]3[CH2:30][CH2:29][C@H:28]([CH2:31][CH2:32][CH3:33])[CH2:27][CH2:26]3)[C:17]([F:22])=[C:18]2[F:21])=[CH:13][CH:12]=1)[CH2:7][CH2:8][CH3:9].O.O.[I:36](O)(=O)(=O)=O.II>C(O)(=O)C.O>[CH2:6]([O:10][C:11]1[C:20]([I:36])=[C:19]2[C:14]([CH:15]=[C:16]([CH2:23][CH2:24][C@H:25]3[CH2:30][CH2:29][C@H:28]([CH2:31][CH2:32][CH3:33])[CH2:27][CH2:26]3)[C:17]([F:22])=[C:18]2[F:21])=[CH:13][CH:12]=1)[CH2:7][CH2:8][CH3:9]

Participants

7

Reactant 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 86590690HCID 86590690, compoundHCID 178450059HCID 178450059, compound

Product 1

HCID 178450060HCID 178450060, compoundYield 378.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Procedure

(The following is performed in a draft chamber.) A mixture of concentrated sulfuric acid (1.5 ml), water (10 ml), and glacial acetic acid (50 ml) was dropped for about 10 minutes into a suspension of 7-butoxy-3-[2-(trans-4-propylcyclohexyl)ethyl]-1,2-difluoronaphthalene(21.4 g, 0.053 mol), periodic acid dihydrate (2.6 g, 0.011 mol), and iodine (5.4 g, 0.021 mol) in glacial acetic acid (100 ml) with vigorously stirring. After stirring at 60° C. for 4 hours, the reaction liquid was cooled, poured into water, and the reaction was terminated. The precipitated solid was dissolved with toluene, the organic layer was separated, and was extracted with toluene from the aqueous layer. After collecting organic layers, it was rinsed, in order, with 10% sodium thiosulfate aqueous solution, with saturated sodium hydrogen carbonate aqueous solution, and with saturated brine, and was dried with anhydrous sodium sulfate. A light yellow solid (21.4 g) was obtained by removing the solvent under reduced pressure and by recrystallizing the obtained orange solid (from acetone). (Yield 73.9%)

Workup

  1. stirringAfter stirring at 60° C. for 4 hours
  2. customthe reaction liquid
  3. temperaturewas cooled
  4. customthe reaction was terminated
  5. dissolutionThe precipitated solid was dissolved with toluene
  6. customthe organic layer was separated
  7. extractionwas extracted with toluene from the aqueous layer
  8. customAfter collecting organic layers, it
  9. washwas rinsed, in order, with 10% sodium thiosulfate aqueous solution, with saturated sodium hydrogen carbonate aqueous solution
  10. dry with materialwith saturated brine, and was dried with anhydrous sodium sulfate

Sources & evidence

ORD record
ord-d34bca9701f9467f848845fc80319a6c
Source dataset
uspto-grants-2011_04
Patent number
US07919154B2

Reaction notes

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