2-[2-(4-Fluorophenyl)ethenyl]-5-fluorobenzonitrile → 2-[2-(4-Fluorophenyl)ethyl]-5-fluorobenzonitrile

HRID 8396Notes

Reaction equation

HRID 8396 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:11]=2[C:12]#[N:13])=[CH:4][CH:3]=1>COCCOC.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:11]=2[C:12]#[N:13])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 541251222-[2-(4-Fluorophenyl)ethenyl]-5-fluorobenzonitrile

Product 1

HCID 220157642-[2-(4-Fluorophenyl)ethyl]-5-fluorobenzonitrileYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-[2-(4-Fluorophenyl)ethenyl]-5-fluorobenzonitrile (2.1 g, 8.7 mmol) was dissolved in ethylene glycol dimethyl ether (100 mL). Palladium on charcoal (10% Pd; 0.20 g) was added, and the reaction mixture was shaken under 60 psig H2 for 1 h. The reaction mixture was then filtered through Celite®, and the filtrate was rotary evaporated (75° C.) to provide 2.1 g (99%) of product as a light-yellow oil.

Workup

  1. filtrationThe reaction mixture was then filtered through Celite®
  2. customthe filtrate was rotary evaporated (75° C.)

Sources & evidence

ORD record
ord-aab5917117c346febea6a78881833188
Source dataset
uspto-grants-2006_08
Patent number
US07087765B2

Reaction notes

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