2-Propenoic acid, 3-iodo-, 1-methylethyl ester, (2Z)- synthesis

Yield: 83.5%

Reaction Conditions:

with acetic acid;sodium iodide at 25 - 115; for 1.5 h;

Steps:

28 Synthesis of (Z)-isopropyl 3-iodoacrylate.
Synthesis of (Z)-isopropyl 3-iodoacrylate. To a mixture of isopropyl propiolate (350g, 3.1 moles ) in AcOH (1300 mL) was added Nal (930 g, 6.2 moles) at 25 °C. The reaction mixture was heated to 115 °C and stirred for 1.5 hrs. The reaction mixture was cooled to 25 to 30 °C and quenched with water followed by extraction with MTBE. The organic layer was washed with saturated bicarbonate, bisulfite and brine solution. The organic layer was dried over sodium sulfate and concentrated under vacuum to give the product (Z)-isopropyl 3-iodoacrylate (626 g; 83.5%). Product was confirmed by 1H NMR.

References:

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