Styrene → 1-Iodo-3-(2-phenylethenyl)benzene

HRID 1156248Notes

Reaction equation

HRID 1156248 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=O.C=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(C(C)C)C(C)C)C>C(#N)CC>[I:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 7501StyreneHCID 743783-Iodobenzoyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 536492591-Iodo-3-(2-phenylethenyl)benzeneYield 10%

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Procedure

The procedure described in Example 1 is followed, except that 26.65 g (0.1 mol) of 3-iodobenzoyl chloride, 13 g (0.125 mol) of styrene, 12.93 g (0.1 mol) of ethyl-diisopropylamine and 0.575 g (0.001 mol) of bis-(dibenzylidene-acetone)-palladium(O) are used. After a reaction time of 3 hours at the reflux temperature in 150 ml of propionitrile, 3.05 g (0.01 mol) of 3-iodostilbene, corresponding to a yield of 10% of theory, are obtained; melting point 96° C.

Sources & evidence

ORD record
ord-f0159cd22845436da46e550600ac95f0
Source dataset
uspto-grants-1982_06
Patent number
US04335055

Reaction notes

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