Water → HCID 15229342, compound

HRID 2396411Notes

Reaction equation

HRID 2396411 reaction equation
[CH:1]1[C:2]([I:10])=[CH:3][C:4]([I:9])=[C:5]([OH:8])[C:6]=1[I:7].[H-].[Na+].CS(O[CH2:18][CH2:19][CH:20]([O:22]S(C)(=O)=O)[CH3:21])(=O)=O.O>CN(C=O)C.C(OCC)(=O)C>[I:7][C:6]1[CH:1]=[C:2]([I:10])[CH:3]=[C:4]([I:9])[C:5]=1[O:8][CH2:18][CH2:19][CH:20]([O:22][C:1]1[C:6]([I:7])=[CH:5][C:4]([I:9])=[CH:3][C:2]=1[I:10])[CH3:21]

Participants

7

Reactant 4

HCID 962WaterHCID 118622,4,6-TriiodophenolHCID 24758Sodium hydrideHCID 997953-Methylsulfonyloxybutyl methanesulfonate

Product 1

HCID 15229342HCID 15229342, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of triiodophenol (5.78 g, 12.3 mmol) and sodium hydride (0.49 g, 60% dispersion, 12.3 mmol) in DMF (15 ml) was stirred at room temperature for 1 hour and then a solution of 1,3-bis-(methanesulfonyloxy) butane (1.37 g, 5.58 mmol) in DMF (5 ml) was added. The mixture was heated to 90° C. for 6 hours and then poured into water after cooling. Ethyl acetate was added and the mixture was allowed to stand overnight. The precipitated solid was collected and dried to give 3.0 g (54%) of the desired product, Mp 173°-175° C.

Workup

  1. temperatureThe mixture was heated to 90° C. for 6 hours
  2. temperatureafter cooling
  3. waitto stand overnight
  4. customThe precipitated solid was collected
  5. customdried

Sources & evidence

ORD record
ord-7f64079623574a23894b0d82f882cfb5
Source dataset
uspto-grants-1996_02
Patent number
US05492687

Reaction notes

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