Potassium Hydroxide → HCID 57567904, compound

HRID 914535Notes

Reaction equation

HRID 914535 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:19]3=[C:20]4[C:10](=[C:11]([CH3:35])[CH:12]=[C:13]([C:21]5[C:22]6[C:27]([CH:28]=[C:29]7[C:34]=5[CH:33]=[CH:32][CH:31]=[CH:30]7)=[CH:26][CH:25]=[CH:24][CH:23]=6)[C:14]4=[CH:15][CH:16]=[C:17]3[CH:18]=1)[CH:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].[Br:38]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCOCC1.O>[Br:38][C:28]1[C:29]2[C:34]([C:21]([C:13]3[C:14]4[C:20]5=[C:19]6[C:17](=[CH:16][CH:15]=4)[CH:18]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=[C:7]6[CH:8]=[CH:9][C:10]5=[C:11]([CH3:35])[CH:12]=3)=[C:22]3[C:27]=1[CH:26]=[CH:25][CH:24]=[CH:23]3)=[CH:33][CH:32]=[CH:31][CH:30]=2

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 24408BromineHCID 24477Sodium ThiosulfateHCID 57567899HCID 57567899, compound

Product 1

HCID 57567904HCID 57567904, compoundYield 50.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

Under a nitrogen atmosphere, Intermediate Compound 1 (6 g, 13.4 mmol) was dissolved in 100 ml of dioxane. An aqueous solution prepared by dissolving 0.75 g (13.4 mmol) of potassium hydroxide in 5 ml of distilled water was added to the solution, and 2.56 g (16.1 mmol) of bromine were dropped to the mixture. After the resultant had been stirred on an oil bath heated to 40° C. for 30 minutes, 9.7 g (3.08 mmol) of a 5% sodium thiosulfate solution were added to the resultant, and the whole was stirred at 20° C. for an additional 2 hours. After having been filtrated, the resultant was washed with methanol and recrystallized from toluene (twice). The resultant was dried in a vacuum under heat, whereby 3.6 g of Intermediate Compound 2 were obtained.

Workup

  1. customAn aqueous solution prepared
  2. additionwere dropped to the mixture
  3. stirringthe whole was stirred at 20° C. for an additional 2 hours
  4. filtrationAfter having been filtrated
  5. washthe resultant was washed with methanol
  6. customrecrystallized from toluene (twice)
  7. customThe resultant was dried in a vacuum
  8. temperatureunder heat

Sources & evidence

ORD record
ord-809b999a65374ffc8aece450cc1fe910
Source dataset
uspto-grants-2011_09
Patent number
US08026664B2

Reaction notes

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