Iodine → 4-Chloro-8-(trifluoromethyl)quinoline

Participants

Reaction Steps

13.75 g of monosublimated iodine were added at 0° to 5° C. to75 ml of phosphorus oxychloride and the mixture was heated over 30 minutes to 93°-95° C. and was held at 93°-95° C. for about 30 minutes. Then, 50 g of the product of Step A were added over 6 minutes in fractions of 1.250 g to the mixture and then the mixture was held at 93°-95° C. for 30 minutes. After cooling to 70°±5° C., the mixture was added over about 30 minutes toa stirred solution of 11 g of sodium bisulfite in 875 ml of water held at 40° to 45° C. The mixture was cooled over 30 minutes to 15°-20° C. to obtain a gummy suspension which was vacuum filtered washed and dried. The product was crystallized from methanol to obtain 36.9 g of 4-chloro-8-trifluoromethyl-quinoline with a 98% purity.

Provenance & Evidence