Acrylonitrile → HCID 118005978, compound

HRID 1049619Notes

Reaction equation

HRID 1049619 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[Cl:5][C:6]1[CH:11]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])[CH:9]=[C:8](I)[CH:7]=1.CCN(CC)CC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[Cl:5][C:6]1[CH:7]=[C:8](/[CH:3]=[CH:2]\[C:1]#[N:4])[CH:9]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])[CH:11]=1.[Cl:5][C:6]1[CH:7]=[C:8](/[CH:3]=[CH:2]/[C:1]#[N:4])[CH:9]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])[CH:11]=1

Participants

7

Reactant 3

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 118005931HCID 118005931, compound

Product 2

HCID 118005977HCID 118005977, compoundYield 16%HCID 118005978HCID 118005978, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

Acrylonitrile (1.6 mL, 41 mmol) was added to a mixture of 9 (1.5 g, 4.1 mmol), Et3N (1.1 mL, 13 mmol), PdCl2(PPh3)2 (0.16 g 0.23 mmol), and dry DMF (15.0 mL) under a nitrogen atmosphere at room temperature. The mixture was heated at 140° C. for 3 h. The reaction mixture was quenched with water and extracted with EtOAc (3×50 mL). The organic layer was sequentially washed with brine (2×75 mL), dried over anhydrous Na2SO4, concentrated by rotary evaporation, and purified by column chromatography to give (Z)-3-(3-chloro-5-(2-methoxyphenoxy)phenyl)acrylonitrile (0.17 g, 16%) and (E)-3-(3-chloro-5-(2-methoxyphenoxy)phenyl)acrylonitrile (10) (0.52 g, 45%). 1H NMR (400 MHz, CDCl3) δ 7.27 (s, 1H), 7.19-7.08 (m, 2H), 7.06-6.97 (m, 2H), 6.91 (ddt, J=15.9, 14.2, 4.6 Hz, 3H), 5.80 (dd, J=16.6, 5.2 Hz, 1H), 3.79 (s, 3H).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe organic layer was sequentially washed with brine (2×75 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated by rotary evaporation
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-458dc609fc4f47acae3d8e6768854f88
Source dataset
uspto-grants-2016_07
Patent number
US09382245B2

Reaction notes

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