Acrylonitrile → HCID 54377318, compound

HRID 1284869Notes

Reaction equation

HRID 1284869 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)P(=O)(N(C)C)N(C)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 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 12679HexamethylphosphoramideSolvent2×

Conditions

Temperature
130 °C

Procedure

A stock solution consisting of 0.1041 g (1.25×10-4 mol) of diacetato-bis-(tris-o-tolylphosphine)-palladium(II) in 50 ml of hexamethylphosphoric acid triamide is prepared under argon. 1 ml of stock solution, 9.25 g (50 mmols) of 4-bromobenzaldehyde, 3.66 ml (55 mmols) of acrylonitrile and 4.51 g (55 mmols) of anhydrous sodium acetate are added, under argon, to 19 ml of hexamethylphosphoric acid triamide, and the mixture is stirred at 130° C. for 8 hours. The hexamethylphosphoric acid triamide is removed under a high vacuum and the product is distilled. 6.58 g (41.9 mmols) of 4-formylcinnamonitrile are obtained, corresponding to a yield of 84% of theory (conversion figure 16800; Pd content 0.005 mol %).

Workup

  1. customis prepared under argon
  2. customThe hexamethylphosphoric acid triamide is removed under a high vacuum
  3. distillationthe product is distilled

Sources & evidence

ORD record
ord-880982b89d854f7e93954fb110809a4d
Source dataset
uspto-grants-1986_01
Patent number
US04564479

Reaction notes

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