Butyl Acrylate → butyl (E)-3-{3-chloro-5-methyl-4-[(5-nitropyridin-2-yl)oxy]phenyl}prop-2-enoate

HRID 1023354Notes

Reaction equation

HRID 1023354 reaction equation
Br[C:2]1[CH:17]=[C:16]([CH3:18])[C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][N:8]=2)=[C:4]([Cl:19])[CH:3]=1.[C:20]([O:24][CH2:25][CH2:26][CH2:27][CH3:28])(=[O:23])[CH:21]=[CH2:22].C1(CNCC2CCCCC2)CCCCC1.F[B-](F)(F)F.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>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].O.O1CCOCC1>[Cl:19][C:4]1[CH:3]=[C:2](/[CH:22]=[CH:21]/[C:20]([O:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:23])[CH:17]=[C:16]([CH3:18])[C:5]=1[O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][N:8]=1

Participants

8

Reactant 4

HCID 8846Butyl AcrylateHCID 4594378Bis(cyclohexylmethyl)amineHCID 44558591Tri-t-butylphosphine fluoroborateHCID 673279772-(4-Bromo-2-chloro-6-methylphenoxy)-5-nitropyridine

Product 1

HCID 86673386butyl (E)-3-{3-chloro-5-methyl-4-[(5-nitropyridin-2-yl)oxy]phenyl}prop-2-enoate

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a 1,4-dioxane (10 mL) solution of 2-(4-bromo-2-chloro-6-methylphenoxy)-5-nitropyridine (1.00 g) and butyl acrylate (0.480 mL) were added N,N-dicyclohexylmethylamine (0.655 mL), tri-tert-butylphosphine tetrafluoroborate (34 mg) and tris(dibenzylideneacetone)dipalladium (0) (40 mg) at room temperature. The resultant mixture was stirred at 70° C. under a nitrogen atmosphere for 4 hours. To the reaction mixture was added water, and extracted with AcOEt. The organic layer was washed with saturated aqueous NaCl, dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=9/1 to 1/1) to afford butyl (E)-3-{3-chloro-5-methyl-4-[(5-nitropyridin-2-yl)oxy]phenyl}prop-2-enoate as a yellow powder (1.05 g).

Workup

  1. extractionextracted with AcOEt
  2. washThe organic layer was washed with saturated aqueous NaCl
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=9/1 to 1/1)

Sources & evidence

ORD record
ord-79311348b70c47f6bd0f45b6b12a9c89
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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