1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-Methoxy-4-(pentafluoro-lambda~6~-sulfanyl)benzene

HRID 2080937

Reaction equation

HRID 2080937 reaction equation
[F:1][S:2]([F:13])([F:12])([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[CH2:14]1CCN2C(=NCCC2)CC1>C(=O)(OC)OC.CC(=O)OCC>[CH3:14][O:9][C:6]1[CH:7]=[CH:8][C:3]([S:2]([F:10])([F:11])([F:12])([F:13])[F:1])=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27792034-Hydroxyphenylsulfur pentafluoride

Product 1

HCID 596421411-Methoxy-4-(pentafluoro-lambda~6~-sulfanyl)benzeneYield 41.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 12021Dimethyl CarbonateSolvent

Procedure

5.00 g of 4-pentafluorosulfanylphenol were dissolved in 50.00 g of dimethyl carbonate and 3.46 g of DBU were added. The mixture was boiled under reflux for 10 hours, then allowed to cool and diluted with 200 ml of EA. Subsequently, the mixture was washed twice with 100 ml each time of a 5% aqueous HCl solution, then with 100 ml of a 5% aqueous NaOH solution. Drying was effected over MgSO4 and the solvent was removed under reduced pressure. Chromatography on silica gel using 1:1 DIP/HEP afforded 2.2 g of a colorless oil.

Workup

  1. temperatureunder reflux for 10 hours
  2. temperatureto cool
  3. washSubsequently, the mixture was washed twice with 100 ml each time of a 5% aqueous HCl solution
  4. customDrying
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ef5689f16adc46ed85f114b2649afa4f
Source dataset
uspto-grants-2011_04
Patent number
US07932416B2

Linked notes

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