1,1'-Carbonyldiimidazole → HCID 66961495, compound

HRID 2364633Notes

Reaction equation

HRID 2364633 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:11])[CH2:9][OH:10])=[CH:4][CH:3]=1.[C:12](N1C=CN=C1)(N1C=CN=C1)=[O:13]>C(#N)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][O:10][C:12](=[O:13])[O:11]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 111486511-(4-bromophenyl)ethane-1,2-diol

Product 1

HCID 66961495HCID 66961495, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

1-(4-bromophenyl)ethane-1,2-diol (0.15 g, 0.69 mmol) was dissolved in 7 mls of dry acetonitrile, followed by the addition of carbonyldiimidazole (0.17 g, 1.04 mmol). This mixture was warmed to 40° C. for 1.5 hours. After cooling to room temperature, the reaction mixture was diluted with EtOAc and washed with saturated ammonium chloride solution, water, dried over sodium sulfate and concentrated under reduced pressure. 10 g Sep Pak purification (1:1 EtOAc:Hexanes) afforded 0.095 g of 4-(4-bromophenyl)-1,3-dioxolan-2-one (57%) as a white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with saturated ammonium chloride solution, water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. custom10 g Sep Pak purification (1:1 EtOAc:Hexanes)

Sources & evidence

ORD record
ord-c17463886e1348248779e1cc9915aedd
Source dataset
uspto-grants-2014_04
Patent number
US08691809B2

Reaction notes

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