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

HRID 2081311Notes

Reaction equation

HRID 2081311 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1Br)[CH3:2].C([Sn](CC[CH2:43][CH3:44])(CCCC)/C=C/[Sn](CCCC)(CCCC)CCCC)CCC.[I:45]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>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1/[CH:44]=[CH:43]/[I:45])[CH3:2]

Participants

7

Reactant 3

HCID 807IodineHCID 5378370trans-1,2-Bis(tri-n-butylstannyl)ethyleneHCID 150701144-(2-Bromophenoxy)butyric acid ethyl ester

Product 1

HCID 150701204-[2-[(E)-2-iodovinyl]-phenoxy]butyric acid ethyl esterYield 75%

Reagents, catalysts & solvents 3

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

Procedure

861 mg of 4-(2-bromophenoxy)-butyric acid ethyl ester and 4.8 g of (E)-1,2-bis-(tri-n-butylstannyl)-ethylene (50%) are dissolved in 11 ml of toluene, mixed with 70 mg of tetrakis-(triphenylphosphine)-palladium and heated with stirring and under argon atmosphere for 1 hour to 120° C. (bath temperature). After cooling to room temperature, the reaction mixture is diluted with 9 ml of diethyl ether and mixed at 0° C. with a solution of 1.53 g of iodine in 7 ml of diethyl ether. The mixture is stirred for 2 hours at 0° C. and allowed to stand overnight in a refrigerator. The batch is concentrated by evaporation and the residue is chromatographed on silica gel with n-hexane/ethyl acetate=95/5. 810 mg of 4-[2-[(E)-2-iodovinyl]-phenoxy]-butyric acid ethyl ester is obtained as an oily crude product, which is further reacted without further purification.

Workup

  1. temperatureheated
  2. stirringThe mixture is stirred for 2 hours at 0° C.
  3. concentrationThe batch is concentrated by evaporation
  4. customthe residue is chromatographed on silica gel with n-hexane/ethyl acetate=95/5

Sources & evidence

ORD record
ord-ad9f42c333444e65a5b68150132b5bb3
Source dataset
uspto-grants-1993_02
Patent number
US05183925

Reaction notes

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