Styrene → HCID 5162089, compound

HRID 2073641Notes

Reaction equation

HRID 2073641 reaction equation
[C:1]1([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([C:7](Cl)=[O:8])=[CH:3][CH:2]=1.BrC1C=CC(C(O)=[O:24])=CC=1.C=CC1C=CC=CC=1.C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Cl>[C:1]1([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([C:7]([OH:24])=[O:8])=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 7501StyreneHCID 8471TriethylamineHCID 114644-Bromobenzoic acidHCID 538172884-(2-Phenylethenyl)benzoyl chloride

Product 1

HCID 5162089HCID 5162089, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 313Hydrochloric AcidSolvent

Procedure

Stilbene-4-carboxylic acid chloride can be prepared as follows: 25.15 g (125 mmols) of 4-bromobenzoic acid, 16.25 g (156.25 mmols) of styrene, 26.55 g (262.5 mmols) of triethylamine, 0.28 g (1.25 mmols) of palladium acetate and 1.52 g (5 mmols) of tri-o-tolylphosphine are stirred at 100° C. for 3.5 hours. The reaction mixture is poured into 100 ml of 2N HCl and the crude product is filtered off and recrystallised from tetrahydrofuran/toluene. 15.3 g (55% of theory) of stilbene-4-carboxylic acid are obtained in the form of white crystals; melting point 252.4° C.

Workup

  1. filtrationthe crude product is filtered off
  2. customrecrystallised from tetrahydrofuran/toluene

Sources & evidence

ORD record
ord-39455c6a9dd84a149c30a8fe2ef0ba3a
Source dataset
uspto-grants-1990_04
Patent number
US04918215

Reaction notes

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