Sodium Hydroxide → 3-(4-(3-(Trifluoromethyl)phenoxy)phenyl)acrylonitrile

HRID 474601Notes

Reaction equation

HRID 474601 reaction equation
[Br-].[C:2]([CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:3].[OH-].[Na+].[F:26][C:27]([F:44])([F:43])[C:28]1[CH:29]=[C:30]([CH:40]=[CH:41][CH:42]=1)[O:31][C:32]1[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=1>O.C(Cl)Cl>[F:26][C:27]([F:44])([F:43])[C:28]1[CH:29]=[C:30]([CH:40]=[CH:41][CH:42]=1)[O:31][C:32]1[CH:39]=[CH:38][C:35]([CH:36]=[CH:4][C:2]#[N:3])=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 11811037(Cyanomethyl)triphenylphosphonium bromideHCID 121487884-(3-(Trifluoromethyl)phenoxy)benzaldehyde

Product 1

HCID 677761303-(4-(3-(Trifluoromethyl)phenoxy)phenyl)acrylonitrileYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (cyanomethyl)triphenylphosphonium bromide (8.61 g, 22.54 mmol) and NaOH (1.127 g, 28.2 mmol) in water (24 mL) and DCM (12 mL) was added 4-(3-(trifluoromethyl)phenoxy)benzaldehyde (5 g, 18.78 mmol) at 0° C. The mixture was stirred at room temperature for 4 h. DCM (50 mL) and water (50 mL) was added to the mixture, the organic phase was washed with water (50 mL), brine (50 mL), dried over anhydrous sodium sulfate and concentrated. Purification via flash chromatography afforded the title compound (5.07 g, 17.26 mmol, 92% yield) as pale yellow oil (slowly solidify to white solid). LCMS: rt=1.67 min, [M+H+]=290

Workup

  1. washthe organic phase was washed with water (50 mL), brine (50 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customPurification via flash chromatography

Sources & evidence

ORD record
ord-003e77e241f74e9f90b53704c42d9361
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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