Tetrahydrofuran → 5-Ethenyl-2-{[3-(trifluoromethyl)phenyl]oxy}benzonitrile

HRID 705873Notes

Reaction equation

HRID 705873 reaction equation
[H-].[Na+].[CH:3]([C:5]1[CH:6]=[CH:7][C:8]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[C:9]([CH:12]=1)[C:10]#[N:11])=O.[CH2:24]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:3]([C:5]1[CH:6]=[CH:7][C:8]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[C:9]([CH:12]=1)[C:10]#[N:11])=[CH2:24]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 86666203Benzonitrile, 5-formyl-2-[3-(trifluoromethyl)phenoxy]-

Product 1

HCID 668253685-Ethenyl-2-{[3-(trifluoromethyl)phenyl]oxy}benzonitrileYield 50.3%

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

To a solution of methyltriphenylphosphonium bromide (11.78 g, 33.0 mmol) in dry THF (100 mL) was added dropwise a solution of NaH (4.79 g, 110 mmol) in THF (100 mL) under nitrogen for 0.5 h. Then a solution of 5-formyl-2-{[3-(trifluoromethyl)phenyl]oxy}benzonitrile (8 g, 27.5 mmol) in THF (1 mL) was added slowly into the reaction mixture. The mixture was then allowed to warm to room temperature and stirring continued for 2 h. Purification via flash chromatography then afforded the title compound (4 g, 13.83 mmol, 50.3% yield).

Workup

  1. customPurification via flash chromatography

Sources & evidence

ORD record
ord-75d5dbb44a3d4174bd266047aced099e
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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