Styrene → 5-Chloro-2-methoxy-beta-phenylstyrene

HRID 644447

Reaction equation

HRID 644447 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[CH2:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([O:9][CH3:10])=[C:2]([CH:7]=1)[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 7501StyreneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 5219352-Bromo-4-chloroanisole

Product 1

HCID 685787655-Chloro-2-methoxy-beta-phenylstyreneYield 35.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

Palladium acetate (21 mg, 7 mol %) was added to a solution of 2-bromo-4-chloroanisole (300 mg, 1.4 mmol), styrene (211 mg, 2 mmol), triethylamine (13 μL, 0.1 mmol) and triphenylphosphine (50 mg, 1.9 mmol) in acetonitrile (6 mL), and the mixture was refluxed for 8 hours under argon atmosphere. After the reaction mixture was cooled to room temperature, the solvent was concentrated under reduced pressure and the obtained residue was diluted with ethyl acetate (15 mL). After the solution was washed successively with 2N hydrochloric acid, water and brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=10:1) to give the title compound (118 mg, 35.6%) as a white powder.

Workup

  1. temperaturethe mixture was refluxed for 8 hours under argon atmosphere
  2. concentrationthe solvent was concentrated under reduced pressure
  3. additionthe obtained residue was diluted with ethyl acetate (15 mL)
  4. washAfter the solution was washed successively with 2N hydrochloric acid, water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe residue obtained by evaporation of the solvent under reduced pressure
  7. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-bc323d90db4149c59ce4603da76843ae
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Linked notes

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