Acetic Acid → 1-Bromo-2-fluoro-4-iodobenzene

Participants

Reaction Steps

Sodium nitrite (51.2 g) was dissolved in sulfuric acid (390 ml), and then acetic acid (454 ml) was added thereto at 10° C. or lower. The mixed solution was kept at 20° to 25° C., and 2-fluoro-4-iodoaniline (124 g) was added for 1 hour, followed by stirring for 2 hours. The reaction solution was added dropwise to a mixed solution of copper bromide (130 g) with 48% hydrobromic acid (390 ml), and stirred overnight. Then, water (1000 ml) was added to the solution, and the resulting solution was extracted with chloroform, followed by washing with water 3 times. After distilling off chloroform, the resultant was distilled under reduced pressure (b.p. 120° to 125° C./13 mmHg), and then recrystallized from methanol to give 1-bromo-2-fluoro-4-iodobenzene (114 g).

Provenance & Evidence