Iodine → HCID 178444342, compound

HRID 429710Notes

Reaction equation

HRID 429710 reaction equation
[H-].[Na+].[CH2:3]([C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([SH:22])=S)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[CH2:4][CH2:5][CH2:6][CH3:7].[F:23][C:24]1[C:29]([F:30])=[C:28]([O:31][CH2:32][CH3:33])[CH:27]=[CH:26][C:25]=1[OH:34].II.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1COCC1>[CH2:3]([C@H:8]1[CH2:9][CH2:10][C@H:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20]([O:34][C:25]3[CH:26]=[CH:27][C:28]([O:31][CH2:32][CH3:33])=[C:29]([F:30])[C:24]=3[F:23])=[S:22])=[CH:18][CH:19]=2)[CH2:12][CH2:13]1)[CH2:4][CH2:5][CH2:6][CH3:7]

Participants

7

Reactant 5

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 24758Sodium hydrideHCID 144957634-Ethoxy-2,3-difluorophenolHCID 178444343HCID 178444343, compound

Product 1

HCID 178444342HCID 178444342, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

To a suspension prepared by suspending 1.52 g (38.0 mmol) of 60% sodium hydride in 15 ml of THF was added dropwise solution of 5.29 g (17.3 mmol) of the 4-(trans-4-n-pentylcyclohexyl)-phenyldithiocarboxylic acid obtained by the first step, in 20 ml of THF under a condition cooled with ice in 15 min, and stirred as it was for 30 min. To this reaction solution was added dropwise solution of 2.50 g (14.4 mmol) of 2,3-difluoro-4-ethoxyphenol in 20 ml of THF in 15 min and stirred as it was for 30 min. To this reaction solution was added dropwise solution of 9.64 g (38.0 mmol) of iodine in 20 ml of THF in 15 min, stirred as it was for 1 hour, warmed up to room temperature, and then stirred at the same temperature overnight. This reaction solution was poured into 10% aqueous sodium thiosulfate solution and extracted with 100 ml of diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under a reduced pressure, and the residue was purified by silica gel column chromatography (eluent: heptane) and further recrystallized from heptane to obtain 2.0 g of 2,3-difluoro-4-ethoxyphenyl 4-(trans-4-n-pentylcyclohexyl)thiobenzoate (yield 31.2%).

Workup

  1. customTo a suspension prepared
  2. temperaturecooled with ice in 15 min
  3. stirringstirred as it
  4. waitwas for 30 min
  5. stirringstirred as it
  6. waitwas for 1 hour
  7. stirringstirred at the same temperature overnight
  8. extractionextracted with 100 ml of diethyl ether
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off under a reduced pressure
  11. customthe residue was purified by silica gel column chromatography (eluent: heptane)
  12. customfurther recrystallized from heptane

Sources & evidence

ORD record
ord-fbc2305469954ff2af47ce892fc1cfc4
Source dataset
uspto-grants-2001_11
Patent number
US06319570B1

Reaction notes

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