Allyl bromide → HCID 70185477, compound

HRID 1741002Notes

Reaction equation

HRID 1741002 reaction equation
C([CH:3](O)[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:7]=1)C.C(C1N[CH:27]=[CH:28]N=1)(C1NC=CN=1)=O.C([Br:33])C=C>C(#N)C>[CH2:27]([CH:5]([C:6]1[CH:7]=[CH:8][C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:11]=1)[CH2:4][CH2:3][Br:33])[CH3:28]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 21834382HCID 21834382, compound

Product 1

HCID 70185477HCID 70185477, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The ethyl 3-(4-carboethoxyphenyl)propanol (1.00 g, 4.80 mmol) was dissolved in 8 ml of dry acetonitrile under nitrogen and treated with carbonyl diimidazole (1.01 g, 6.24 mmol). After ten minutes, allyl bromide (1.66 ml, 19.2 mmol) was added and the reaction was refluxed for 5 hours. After cooling, the mixture was evaporated, slurried in water and extracted twice with 5:1 pentane/diethyl ether solution. The organic extracts were washed with water and then brine, dried over MgSO4 and concentrated to afford 1.15 g (88% yield) of the subtitle compound.

Workup

  1. waitAfter ten minutes
  2. temperaturethe reaction was refluxed for 5 hours
  3. temperatureAfter cooling
  4. customthe mixture was evaporated
  5. extractionextracted twice with 5:1 pentane/diethyl ether solution
  6. washThe organic extracts were washed with water
  7. dry with materialbrine, dried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0dbdf0453c4a4dce8b83e6a0243ad315
Source dataset
uspto-grants-1999_10
Patent number
US05972972

Reaction notes

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