Sodium hydride → 1-(Trifluoromethyl)-3-(4-vinylphenoxy)benzene

HRID 474584Notes

Reaction equation

HRID 474584 reaction equation
[H-].[Na+].[F:3][C:4]([F:21])([F:20])[C:5]1[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=1)[O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1.[I-].[CH3:23][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[F:3][C:4]([F:21])([F:20])[C:5]1[CH:19]=[CH:18][CH:17]=[C:7]([O:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[CH2:23])=[CH:11][CH:10]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 638159Methyltriphenylphosphonium iodideHCID 121487884-(3-(Trifluoromethyl)phenoxy)benzaldehyde

Product 1

HCID 677746121-(Trifluoromethyl)-3-(4-vinylphenoxy)benzeneYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (23.66 g, 592 mmol) was added to the solution of 4-(3-(trifluoromethyl)phenoxy)-benzaldehyde (25 g, 94 mmol) and methyltriphenylphosphonium iodide (36.2 g, 101 mmol) in THF (180 mL) at 0° C. The reaction mixture was stirred at room temperature overnight. Purification via a flash column chromatography then afforded the title compound as a colorless oil (24.4 g, 98% yield).

Workup

  1. customPurification via a flash column chromatography

Sources & evidence

ORD record
ord-4376d12d230944d28ad718c22ff70db5
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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