Sodium Sulfite → (S)-1-(2-Bromo-6-methyl-4-nitrophenyl)ethane-1,2-diol

Participants

Reaction Conditions

Reaction Steps

The reaction mixture of 1-bromo-3-methyl-5-nitro-2-vinylbenzene (65C) (12.3 g, 50.83 mmol), AD-mix a (71 g), MeSO2NH2 (4.8 g, 50.8 mmol) in t-butyl alcohol/H2O (1:1) (200 ml) was stirred at 0° C. for 3 days. Na2SO3 (˜6 g) was added to quench the reaction, stirred at rt for 40 min. The reaction mixture was washed by water, extracted by EtOAc, dry over MgSO4, filtered, concentrated down and purified by silica gel column, eluting by 0-100% EtOAc in Hexanes to give 6.96 g of 65D and recovered 2.3 g of 65C.

Provenance & Evidence