Butyl Acrylate → HCID 67327332, compound

HRID 1023340Notes

Reaction equation

HRID 1023340 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Cl:9])[CH:3]=1.[C:10]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:13])[CH:11]=[CH2:12].CN(C1CCCCC1)C1CCCCC1.F[B-](F)(F)F.C([PH+](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].O1CCOCC1>[Cl:9][C:4]1[CH:3]=[C:2](/[CH:12]=[CH:11]/[C:10]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:13])[CH:7]=[CH:6][C:5]=1[OH:8]

Participants

7

Reactant 4

HCID 8846Butyl AcrylateHCID 198594-Bromo-2-chlorophenolHCID 24210N-Methyl dicyclohexylamineHCID 2734635Tri-tert-butylphosphine tetrafluoroborate

Product 1

HCID 67327332HCID 67327332, compound

Reagents, catalysts & solvents 2

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

Procedure

To a dioxane (10 mL) solution of 4-bromo-2-chlorophenol (207 mg) were added n-butyl acrylate (0.158 mL), N-methyldicyclohexylamine (0.236 mL), tri-tert-butylphosphonium tetrafluoroborate (12 mg), and tris(dibenzylideneacetone)dipalladium (0) (18 mg) under a N2 atmosphere. The resultant mixture was refluxed over night. After cooling, the reaction mixture was filtered off on Celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=4/1 to 2/1) to afford butyl (E)-3-(3-chloro-4-hydroxyphenyl)prop-2-enoate (244 mg) as a colorless oil.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered off on Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=4/1 to 2/1)

Sources & evidence

ORD record
ord-4ba6c16c0f13483fbb7948726d4b1b8f
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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