tert-Butanol → (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 (30.0 g, 0.124 mol), AD-mix α (173.5 g: 0.104 g of K2OsO4.2H2O; 1.389 g of (DHQ)2PHAL; 51.038 g of K2CO3 and 120.99 g of K4Fe(CN)6), MeSO2NH2 (11.8 g, 0.124 mol) in t-BuOH (250 mL) and H2O (250 mL) was stirred at 0° C. for 3 days. Na2SO3 (15 g) was added and stirred at room temperature for 40 min to quench the reaction. The reaction mixture was treated with water (1 L) and the resulting mixture was extracted with EtOAc (3×200 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated in vacuo, and purified by silica gel column (Petroleum Ether:EtOAc (2:1), isocratic) to afford (S)-1-(2-Bromo-6-methyl-4-nitrophenyl)ethane-1,2-diol (17 g, 50%) as yellow solid. 1H-NMR: 400 MHz, (CDCl3) δ: 8.26 (s, 1H), 7.99 (s, 1H), 5.56-5.54 (m, 1H), 3.94-3.92 (m, 1H), 3.81-3.78 (m, 1H), 2.82 (d, broad, 1H), 2.67 (s, 3H), 2.18-2.15 (m, 1H).

Provenance & Evidence