Water → 3,3-Diphenyl-1-(2,4,6-triiodophenoxy)propane

HRID 974745

Reaction equation

HRID 974745 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([I:9])[C:3]=1[OH:10].C(=O)([O-])[O-].[K+].[K+].[C:17]1([CH:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:24][CH2:25]Br)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C)C=O.C(OCC)(=O)C>[C:17]1([CH:23]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:24][CH2:25][O:10][C:3]2[C:2]([I:1])=[CH:7][C:6]([I:8])=[CH:5][C:4]=2[I:9])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 118622,4,6-TriiodophenolHCID 883331,1'-(3-Bromopropylidene)bisbenzene

Product 1

HCID 153433153,3-Diphenyl-1-(2,4,6-triiodophenoxy)propaneYield 48.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2,4,6-triiodophenol (0.78 g, 1.65 mmol) and potassium carbonate (0.25 g, 1.82 mmol, 1.1 eq) in 5 ml of dimethylformamide was heated at 60° C. for 1 hr, cooled and then 3,3-diphenylpropyl bromide (0.5 g, 1.82 mmol) was added. After stirring for 30 minutes at room temperature the mixture was heated at 60° C. for 24 hrs. The mixture was then cooled, poured into water and the crude product was isolated by ethyl acetate extraction. The product was purified by silica gel chromatography (2.5% ethyl acetate-hexanes) followed by recrystallization from hexanes to give 0.53 g (48%) of a solid. Mp: 120°-121° C.

Workup

  1. temperaturecooled
  2. temperaturewas heated at 60° C. for 24 hrs
  3. temperatureThe mixture was then cooled
  4. customThe product was purified by silica gel chromatography (2.5% ethyl acetate-hexanes)
  5. customfollowed by recrystallization from hexanes

Sources & evidence

ORD record
ord-f3bdaa27130a4c3ebdbf3b2397b76b13
Source dataset
uspto-grants-1997_03
Patent number
US05607660

Linked notes

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