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

HRID 1798332

반응식

HRID 1798332 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매3회HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-344fc3e33461412d8882f113fcae80b2
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343953B2

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