Sodium Hydroxide → 3-(4-(4-Fluorophenoxy)phenyl)acrylonitrile

HRID 474597Notes

Reaction equation

HRID 474597 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]1[CH:41]=[CH:40][C:30]([O:31][C:32]2[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=2)=[CH:29][CH:28]=1>O.C(Cl)Cl>[F:26][C:27]1[CH:41]=[CH:40][C:30]([O:31][C:32]2[CH:39]=[CH:38][C:35]([CH:36]=[CH:4][C:2]#[N:3])=[CH:34][CH:33]=2)=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 38568024-(4-Fluorophenoxy)benzaldehydeHCID 11811037(Cyanomethyl)triphenylphosphonium bromide

Product 1

HCID 677758203-(4-(4-Fluorophenoxy)phenyl)acrylonitrileYield 91.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (cyanomethyl)triphenylphosphonium bromide (10.61 g, 27.8 mmol) and NaOH (1.387 g, 34.7 mmol) in water (30 mL) and DCM (15 mL) was added 4-(4-fluorophenoxy)benzaldehyde (5 g, 23.13 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 (5.1 g, 21.09 mmol, 91% yield) as white solid. LCMS: rt=1.60 min, [M+H+]=240

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-58c800d8368d4a719edee3c36e8d516d
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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