Styrene → trans-4-Nitrostilbene

HRID 1975874Notes

Reaction equation

HRID 1975874 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.C1(=O)OC(C)CO1>[Pd].C(OCC)C.ClCCl>[CH:16]1[CH:17]=[CH:18][C:13](/[CH:12]=[CH:11]/[C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 7501StyreneHCID 7924Propylene CarbonateHCID 8471TriethylamineHCID 114661-Bromo-4-nitrobenzene

Product 1

HCID 639659trans-4-Nitrostilbene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21881112Ethyl ether methylene chlorideSolvent

Conditions

Temperature
130 °C

Procedure

Under argon, a solution containing 218 mg of p-nitrobromobenzene, 141 mg of styrene, 0.3 ml of triethylamine, and 1 ml of propylene carbonate stabilized colloid solution with a palladium content of 4.023 mg is heated at 130° C. with stirring in a sealed vessel for 4.5 h. At the end of the reaction, 2 ml of diethyl ether/dichloromethane (1:1) is added, and the mixture is filtered. The yield of desired product as determined by GC is 96%.

Workup

  1. additionis added
  2. filtrationthe mixture is filtered

Sources & evidence

ORD record
ord-4c8aaa9901004aebb8e3b679aa3f2986
Source dataset
uspto-grants-2001_05
Patent number
US06224739B1

Reaction notes

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