Iodine → 2-Iodo-3-(4-methoxyphenylsulfonyl)propionic acid

Participants

Reaction Steps

Added water (0.85 grams, 0.85 ml) followed by the acrylic acid (3.42 grams, 3.25 ml), then I2 (12.04 grams, 47.41 mmol) to a slurry of sodium (4-methoxybenzenesulfinate (9.11 grams, 46.94 mmol) in methylene chloride (150 ml). Added more methylene chloride (100 ml) so slurry could stir. Stirred at room temperature for weekend. Washed reaction solution with 1N Na2S2O3 (aq) (3×150 ml) until organic layer was colorless. Washed organic layer with brine. Dried (MgSO4), filtered and concentrated in vacuo, to give 4.23 grams (25%) of crude 2-iodo-3-(4-methoxyphenylsulfonyl)propionic acid.

Provenance & Evidence