Benzaldehyde → 2-(3-Bromo-phenyl)-3-phenyl-propionitrile

HRID 2361755Notes

Reaction equation

HRID 2361755 reaction equation
[OH-].[K+].[CH:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:11][C:12]1[CH:13]=[C:14]([CH2:18][C:19]#[N:20])[CH:15]=[CH:16][CH:17]=1.[BH4-].[Na+]>C(O)C.O.CO>[Br:11][C:12]1[CH:13]=[C:14]([CH:18]([CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:19]#[N:20])[CH:15]=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 14797Potassium HydroxideHCID 36023(3-Bromophenyl)acetonitrileHCID 4311764Sodium borohydride

Product 1

HCID 593319812-(3-Bromo-phenyl)-3-phenyl-propionitrileYield 52%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 40% KOH (2.83 g in 5.0 ml of H2O) in ethanol (13 ml) was added to a solution of benzaldehyde (2.85 ml, 28.05 mmol) and 3-bromophenylacetonitrile (5 g, 25.50 mmol) in ethanol (9 ml). The reaction mixture was then stirred at room temperature for 2 hours and the precipitate was collected by suction filtration and washed with cold ethanol (6.68 g, 92%). The crude product (3.45 g, 12.14 mmol) was then dissolved methanol (35 ml) and heated to 65° C. Sodium borohydride (459 mg, 12.14 mmol) was added in portions and the reaction mixture was maintained at this temperature for a further 2 hours. Upon cooling, water (10 ml) was added and the solvent was removed under reduced pressure. The residue was partitioned between water (100 ml) and ethyl acetate (100 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated to afford the desired product (1.80 g, 52%), which was used without purification.

Workup

  1. filtrationthe precipitate was collected by suction filtration
  2. washwashed with cold ethanol (6.68 g, 92%)
  3. temperaturethe reaction mixture was maintained at this temperature for a further 2 hours
  4. temperatureUpon cooling
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was partitioned between water (100 ml) and ethyl acetate (100 ml)
  7. customThe organic layer was separated
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-73e7edd7d23a4070beaa31818cebc2b7
Source dataset
uspto-grants-2014_04
Patent number
US08691806B2

Reaction notes

Loading…