Styrene → 1-Bromo-4-(2-phenylethenyl)benzene

HRID 1156254Notes

Reaction equation

HRID 1156254 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=O)=[CH:4][CH:3]=1.C=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CCCC)CCCC)CCC.CC1C=CC(C)=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7501StyreneHCID 7622TributylamineHCID 7809P-XyleneHCID 685154-Bromobenzoyl chloride

Product 1

HCID 6013891-Bromo-4-(2-phenylethenyl)benzeneYield 51%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

0.448 g (2 millimols) of palladium acetate, 43.88 g (0.2 mol) of 4-bromobenzoyl chloride, 26 g (0.25 mol) of styrene and 37.06 g (0.2 mol) of tri-n-butylamine in 200 mol of p-xylene are stirred for 4 hours at 120° C. After the reaction mixture has been extracted by shaking with 2 N HCl and 2 N NaOH, and dried over magnesium sulfate, the crude product is chromatographed in toluene on silica gel, and is recrystallised from n-hexane. 26.43 g (51% of theory) of 4-bromostilbene are obtained as pale yellow crystals of melting point 137.7° C.

Workup

  1. extractionAfter the reaction mixture has been extracted
  2. dry with materialdried over magnesium sulfate
  3. customthe crude product is chromatographed in toluene on silica gel
  4. customis recrystallised from n-hexane

Sources & evidence

ORD record
ord-bdcb5a4b55b843b0aa79ab7429783a07
Source dataset
uspto-grants-1982_06
Patent number
US04335055

Reaction notes

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