Sodium borohydride → 3-(4-(4-Fluorophenoxy)phenyl)propanenitrile

HRID 705840Notes

Reaction equation

HRID 705840 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH:13]=[CH:14][C:15]#[N:16])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]#[N:16])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 677758203-(4-(4-Fluorophenoxy)phenyl)acrylonitrile

Product 1

HCID 677758123-(4-(4-Fluorophenoxy)phenyl)propanenitrileYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-(4-(4-fluorophenoxyl)phenyl)acrylonitrile (5 g, 20.90 mmol) in ethanol (80 mL) was added NaBH4 (5.44 g, 144 mmol). The mixture was heated at 70° C. overnight. After cooling to room temperature, the reaction mixture was quenched with water (50 mL), and ethanol was removed under reduced pressure. The residue was partitioned between EA (100 mL) and water (50 mL). The organic phase was washed with saturated NaHCO3 solution (80 mL), brine (50 mL), dried over sodium sulfate, concentrated, and purified via flash chromatography to afford the title compound (4.7 g, 16.48 mmol, 79% yield) as a white solid. LCMS: rt=1.55 min, [M+H+]=242

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was quenched with water (50 mL), and ethanol
  3. customwas removed under reduced pressure
  4. customThe residue was partitioned between EA (100 mL) and water (50 mL)
  5. washThe organic phase was washed with saturated NaHCO3 solution (80 mL), brine (50 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. custompurified via flash chromatography

Sources & evidence

ORD record
ord-0f1c2cd9d4984ff399041dca9556c11a
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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