Sodium Hydroxide → (2E)-3-(4-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)-2-propenenitrile

HRID 705806Notes

Reaction equation

HRID 705806 reaction equation
C1(P(=[CH:20][C:21]#[N:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+].[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33]2[CH:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][CH:34]=2)=[CH:28][C:27]=1[C:41]([F:44])([F:43])[F:42]>C(Cl)Cl.O>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33]2[CH:40]=[CH:39][C:36](/[CH:37]=[CH:20]/[C:21]#[N:22])=[CH:35][CH:34]=2)=[CH:28][C:27]=1[C:41]([F:44])([F:43])[F:42]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 85524(Triphenylphosphoranylidene)acetonitrileHCID 866661874-(4-Chloro-3-(trifluoromethyl)phenoxy)benzaldehyde

Product 1

HCID 67775163(2E)-3-(4-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)-2-propenenitrileYield 85.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To the mixture of (triphenylphosphanylidene)acetonitrile (19.8 g, 51.9 mmol) and NaOH (2.59 g, 64.9 mmol) in DCM (30 mL) and water (60 mL) was added 4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}benzaldehyde (13.0 g, 43.2 mmol)) at 0° C. It was stirred at rt for 4 h. Purification via a flash chromatography afforded the title compound as a white solid (12 g).

Workup

  1. customPurification via a flash chromatography

Sources & evidence

ORD record
ord-8044c93ef7444dacaccf0bb483537876
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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