Iodine → 4-[2-[(E)-2-iodovinyl]-phenoxy]butyric acid methyl ester

HRID 2081314Notes

Reaction equation

HRID 2081314 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1Br.C([Sn](CC[CH2:42][CH3:43])(CCCC)/C=C/[Sn](CCCC)(CCCC)CCCC)CCC.[I:44]I>C1(C)C=CC=CC=1.C(OCC)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1/[CH:43]=[CH:42]/[I:44]

Participants

7

Reactant 3

HCID 807IodineHCID 5378370trans-1,2-Bis(tri-n-butylstannyl)ethyleneHCID 150701264-(2-Bromophenoxy)-butyric acid methyl ester

Product 1

HCID 150701274-[2-[(E)-2-iodovinyl]-phenoxy]butyric acid methyl esterYield 65.5%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

Under the conditions of example 2C, 482 mg of 4-(2-bromophenoxy)-butyric acid methyl ester and 3.2 g of (E)-1,2-bis-(tri-n-butylstannyl)-ethylene (50%) in 6 ml of toluene are heated in the presence of 47 mg of tetrakis-(triphenylphosphine)-palladium, diluted with 6 ml of diethyl ether, mixed with a solution of 1.02 g of iodine in 5 ml of diethyl ether, concentrated by evaporation, and the residue is chromatographed on silica gel. 400 mg of 4-[2-[(E)-2-iodovinyl]-phenoxy]butyric acid methyl ester is obtained as an oily crude product, which is used in the next stage without further purification.

Workup

  1. concentrationconcentrated by evaporation
  2. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-646e1bbdca9643b2846206a3487de3c0
Source dataset
uspto-grants-1993_02
Patent number
US05183925

Reaction notes

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