Acrylonitrile → HCID 54377318, compound

HRID 1284857Notes

Reaction equation

HRID 1284857 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10](#[N:13])[CH:11]=[CH2:12].C([O-])(=O)C.[Na+]>CN(C=O)C.[Pd]>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([CH:12]=[CH:11][C:10]#[N:13])=[CH:3][CH:4]=1)=[O:7]

Participants

6

Reactant 3

HCID 7855AcrylonitrileHCID 707414-BromobenzaldehydeHCID 517045Sodium Acetate

Product 1

HCID 54377318HCID 54377318, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
130 °C

Procedure

A stock solution consisting of 0.0260 g (3.125×10-5 mol) of diacetato-bis-(tris-o-tolylphosphine)-palladium(II) in 50 ml of DMF is prepared under argon. 1 ml of stock solution, 4.63 g (25 mmols) of 4-bromobenzaldehyde, 1.83 ml (27.5 mmols) of acrylonitrile and 2.26 g (27.5 mmols) of anhydrous sodium acetate are added to 9 ml of DMF under argon, and the reaction mixture is stirred at 130° C. for 10 hours. 2.86 g (18.2 mmols) of 4-formylcinnamonitrile are obtained, corresponding to a yield of 73% of theory (conversion figure 29200; Pd content 0.0025 mol %).

Workup

  1. customis prepared under argon

Sources & evidence

ORD record
ord-0960ba11086848ca9ecbbe9b308dd5ac
Source dataset
uspto-grants-1986_01
Patent number
US04564479

Reaction notes

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