Nitrogen → 2-(3-Ethoxy-buta-1,3-dienyl)-5-hydroxy-benzonitrile

HRID 1181098Notes

Reaction equation

HRID 1181098 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[C:4]#[N:5].[C:11]([O:15][CH2:16][CH3:17])(=O)[CH:12]=[CH2:13].[CH:18](N(C(C)C)CC)(C)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.N#N>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)CC>[CH2:16]([O:15][C:11](=[CH2:18])[CH:12]=[CH:13][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[C:4]#[N:5])[CH3:17]

Participants

8

Reactant 5

HCID 947NitrogenHCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 153231112-Bromo-5-hydroxybenzonitrile

Product 1

HCID 734148902-(3-Ethoxy-buta-1,3-dienyl)-5-hydroxy-benzonitrileYield 72%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7854PropionitrileSolvent

Procedure

To a stirred solution of 2-bromo-5-hydroxy-benzonitrile (1.4 g, 7.1 mmol), ethyl acrylate (2.12 g, 21.2 mmol), palladium(II) acetate (0.159 g, 7.0 mmol), diisopropylethylamine (0.82 g, 14.1 mmol), and tri-ortho-tolylphosphine (0.430 g, 14.1 mmol) was added propionitrile (50 mL). The reaction was stirred overnight at 80° C. under a stream of N2. The mixture was cooled, filtered, and concentrated. The crude material (3.0 g) was purified by radial chromatography (10-70% EtOAc/hexanes) to give the title compound as a white solid (1.1 g). MS [EI] m/z 216 (M+H)+.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe crude material (3.0 g) was purified by radial chromatography (10-70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-5b3d1a2a5d214dc6b421074bb6afe008
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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