3-(4-bromophenyl)-3-oxopropanenitrile → HCID 10857133, compound

HRID 1192988Notes

Reaction equation

HRID 1192988 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([CH2:8][C:9]#[N:10])=[O:7])=[CH:4][CH:3]=1.C([BH3-])#N.[Na+]>C(O)C.C(O)(=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([OH:7])[CH2:8][C:9]#[N:10])=[CH:11][CH:12]=1

Participants

6

Reactant 2

HCID 7703123-(4-bromophenyl)-3-oxopropanenitrileHCID 5003444Sodium cyanoborohydride

Product 1

HCID 10857133HCID 10857133, compoundYield 98.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of 4-bromobenzoylacetonitrile (500 mg) in ethanol (5 mL) and acetic acid (300 μL) was heated with sodium cyanoborohydride (280 mg) using an 80° C. hot plate for 2 hours. After cooling to ambient temperature, the mixture was diluted with water and concentrated to a syrup, which was diluted with ethyl acetate and washed with water, sat. NaHCO3, and brine. The extract was dried with MgSO4, filtered, and evaporated to provide 510 mg of a cloudy oil, which was filtered through silica gel using 1:1 ethyl acetate/hexane to provide the product (496 mg) as a thick oil.

Workup

  1. customusing an 80° C.
  2. customfor 2 hours
  3. concentrationconcentrated to a syrup, which
  4. additionwas diluted with ethyl acetate
  5. washwashed with water, sat. NaHCO3, and brine
  6. dry with materialThe extract was dried with MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto provide 510 mg of a cloudy oil, which
  10. filtrationwas filtered through silica gel using 1:1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-4d10ee9aa9a2499285bceb219997b5f6
Source dataset
uspto-grants-2014_03
Patent number
US08680315B2

Reaction notes

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