m-Chloroperbenzoic acid → HCID 59699464, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 23 (334.31 g, 1.11 mol) in anhydrous dichloromethane (5.46 L) at −30° C., mCPBA (255.29 g, 1.11 mol) in anhydrous dichloromethane (3.45 L) was added drop-wise over 2 hours. The reaction mixture was stirred at −20 to −25° C. for 3 hours under nitrogen atmosphere. The reaction mixture was quenched with saturated NaHCO3 (5.8 L) at −20° C. The organic layer was separated, washed with water (3×2 L), brine (2 L), dried over Na2SO4and concentrated to provide 358 g of crude desired product. 1H NMR (400 MHz, CD3OD) 2.80 (s, 3 H), 4.34-4.43 (m, 1H), 4.48-4.52 (m, 1H), 4.65-4.70 (m, 2H), 4.72-4.80 (m, 2H), 5.79 (d, J=8 Hz, 1 H), 7.45-7.48 (m, 2 H), 7.58-7.62 (m, 3H), 7.76-7.89 (m, 2H), 8.02-8.10 (m, 2H). The crude material was used directly in the next step.

Provenance & Evidence