Ethyl Acrylate → HCID 86694134, compound

HRID 707250Notes

Reaction equation

HRID 707250 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[CH:14]=[CH2:15].C1(CNCC2CCCCC2)CCCCC1>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2](/[CH:15]=[CH:14]/[C:13]([O:17][CH2:18][CH3:19])=[O:16])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1

Participants

8

Reactant 3

HCID 8821Ethyl AcrylateHCID 792884-Bromo-3-nitroanisoleHCID 4594378Bis(cyclohexylmethyl)amine

Product 1

HCID 86694134HCID 86694134, compoundYield 46.5%

Reagents, catalysts & solvents 4

HCID 2734635Tri-tert-butylphosphine tetrafluoroborateCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

4-Bromo-3-nitroanisole (10.00 g, 43.1 mmol), ethyl acrylate (5.62 mL, 51.7 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.789 g, 0.862 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.500 g, 1.724 mmol), and N,N-dicyclohexylmethylamine (10.10 mL, 51.7 mmol) were mixed in 1,4-dioxane (170 mL) and placed under an argon atmosphere. The reaction mixture was stirred at room temperature for 22 hours. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The combined organic layers were separated, washed with brine, dried over magnesium sulfate, and concentrated. The resulting crude product was purified via silica gel flash column chromatography eluting with 0 to 20% ethyl acetate in hexanes to yield (E)-ethyl 3-(4-methoxy-2-nitrophenyl)acrylate (5.05 g, 20 mmol, 46.5% yield) as an orange solid.

Workup

  1. extractionextracted twice with ethyl acetate
  2. customThe combined organic layers were separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting crude product was purified via silica gel flash column chromatography
  7. washeluting with 0 to 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-2b3e0076a1af469786daee8933260c57
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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