Bromoacetonitrile → HCID 22993355, compound

HRID 1167616Notes

Reaction equation

HRID 1167616 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][CH:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:8][C:7]=2[CH:18]=1.C(=O)([O-])O.[K+].Br[CH2:25][C:26]#[N:27]>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][CH:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:8]([CH2:25][C:26]#[N:27])[C:7]=2[CH:18]=1

Participants

6

Reactant 3

HCID 11534BromoacetonitrileHCID 516893Potassium BicarbonateHCID 22993356HCID 22993356, compound

Product 1

HCID 22993355HCID 22993355, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

The compound obtained in Step B (480 mg; 1.99 mmol) is suspended in 8 ml of water (4 ml/l mmol). Potassium hydrogen carbonate (10 eq.; 19.89 mmol; 1.657 g), tetrabutylammonium bromide (1 eq.; 1.99 mmol; 641 mg) and bromoacetonitrile (8 eq.; 15.91 mmol; 1.11 ml) are then added. The mixture is stirred vigorously at 90° C. for 8 hours. After returning to ambient temperature, the product formed is extracted with dichloromethane. The organic phase is dried over MgSO4, filtered, and then concentrated under reduced pressure. The residue obtained is purified by flash chromatography on silica gel (eluant: PE/AcOEt (8/2)). The title product is obtained in the form of a colourless oil.

Workup

  1. customAfter returning to ambient temperature
  2. customthe product formed
  3. extractionis extracted with dichloromethane
  4. dry with materialThe organic phase is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customis purified by flash chromatography on silica gel (eluant: PE/AcOEt (8/2))

Sources & evidence

ORD record
ord-fe70b06c0392450cb1547cc69920f849
Source dataset
uspto-grants-2003_09
Patent number
US06620809B2

Reaction notes

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