Dichloromethane → HCID 66738924, compound

Participants

Reaction Conditions

Reaction Steps

While the internal temperature of the reactor containing 2.946 kg (5.20 mol) of 1,2,3,4-tetrabenzoyl-L-arabinopyranose was maintained at 0-20° C., 4.21 kg of a 30-33% hydrogen bromide/acetic acid solution was added dropwise thereto, and the mixture was stirred at room temperature for 6 hours. After completion of the reaction, 1.296 liters of dichloromethane was added to the reaction solution, which was then stirred for 30 minutes. Next, the solution was added dropwise to a reactor containing 4.162 liters of purified water, and was stirred for 30 minutes, and then separated into layers. The water layer was back-extracted with 1.296 liters of dichloromethane. The oil layer was washed two times with 0.195 kg of aqueous saturated sodium chloride solution and one time with 0.248 kg of aqueous saturated sodium bicarbonate solution, and then dried with sodium sulfate, and the solvent was removed by concentration. To the concentrated residue, 1.30 liters of dichloromethane was added, the solution was stirred for 2-3 hours, and 6.50 liters of hexane was added thereto. The resulting solution was cooled to 0-5° C., stirred for 3-4 hours, and then filtered. The filtered solids were washed with 2.76 liters of hexane and dried in a vacuum, thus obtaining 1.912 kg (70% yield) of 1-bromo-2,3,4-tribenzoyl-L-arabinopyranose. 1H NMR (CDCl3): δ 8.20˜7.90 (dd, 4H), 7.90˜7.80 (d, 2H), 7.70˜7.20 (m, 9H), 6.93 (d, 1H), 5.97 (dd, 1H), 5.82 (m, 1H), 5.70 (dd, 1H), 4.50 (d, 1H), 4.25 (d, 1H).

Provenance & Evidence