Water → HCID 57542014, compound

HRID 2422231Notes

Reaction equation

HRID 2422231 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])O.[Na+].O>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:24]1(/[CH:23]=[CH:22]/[C:2]2[CH:3]=[C:4]([CH2:8][O:9][C:10]3[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=3)[CH:5]=[CH:6][CH:7]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 4

HCID 962WaterHCID 7501StyreneHCID 516892Sodium BicarbonateHCID 23136270Methyl 4-[(3-bromophenyl)methoxy]benzenepropanoate

Product 1

HCID 57542014HCID 57542014, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 4-[(3-bromophenyl)methoxy]benzenepropanoate (1.0 g, 2.9 mmol), styrene (0.45 g, 4.3 mmol), sodium hydrogencarbonate (0.60 g, 7.2 mmol), tetrabutylammonium chloride (1.6 g, 5.7 mmol) were dissolved in N,N-dimethylformamide (25 mL) and, after argon substitution, palladium acetate (19 mg, 0.086 mmol) was added. The reaction mixture was heated under an argon atmosphere at 100° C. for 18 hrs. The reaction mixture was cooled, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=15:1) to give the title compound (0.63 g, yield 59%) as a white powder.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=15:1)

Sources & evidence

ORD record
ord-9151d0e115cf40d4a60c64e4f4c7902e
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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