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0 °C

1-Chloro-4-iodo-2-vinylbenzene (2.43 g, 9.19 mmol) was dissolved in t-BuOH/H2O (1:1, 60 mL) and then cooled to 0° C. AD-mix-α (11 g) was slowly added. The reaction slowly warmed to rt overnight. Sodium sulfite (11 g) was added and the solution stirred at rt. After 3 h, H2O and CH2Cl2 were added and the organic layer isolated. The aqueous layer was washed with CH2Cl2 (3×) and then the combined organic extracts were combined, dried (Na2SO4), concentrated, and purified by Biotage chromatography (0%-100% EtOAc/hexanes) to afford 2.6 g of (1S)-1-(2-chloro-5-iodophenyl)ethane-1,2-diol as an oil that will solidify over time (95%). 1H NMR (400 MHz, chloroform-d) δ ppm 7.94 (d, J=2.27 Hz, 1 H) 7.55 (dd, J=8.34, 2.02 Hz, 1 H) 7.07 (d, J=8.34 Hz, 1 H) 5.17 (dd, J=7.58, 3.03 Hz, 1 H) 3.90 (dd, J=11.24, 3.16 Hz, 1 H) 3.54 (dd, J=11.24, 7.71 Hz, 1 H) 3.49 (s, 2 H).

1. customThe reaction
2. temperatureslowly warmed to rt overnight
3. customthe organic layer isolated
4. washThe aqueous layer was washed with CH2Cl2 (3×)
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated
7. custompurified by Biotage chromatography (0%-100% EtOAc/hexanes)