Benzaldehyde → HCID 59331981, compound

HRID 45483

Reaction equation

HRID 45483 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>[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

7

Reactant 4

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

Product 1

HCID 59331981HCID 59331981, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 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 in ethanol (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. temperatureheated to 65° C
  4. temperaturethe reaction mixture was maintained at this temperature for a further 2 hours
  5. temperatureUpon cooling
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was partitioned between water (100 ml) and ethyl acetate (100 ml)
  8. customThe organic layer was separated
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-010974ad3b054543a18be438d0ff5066
Source dataset
uspto-grants-2013_09
Patent number
US08541461B2

Linked notes

Loading…