Hydrochloric Acid → 1-Iodo-2-methyl-3-(trifluoromethyl)benzene

Temperatur

0 °C

3-Amino-2-methylbenzotrifluoride (Aldrich Co., 5.25 g) was added to a mixture of concentrated hydrochloric acid (20 ml) and water (20 ml) and, under ice-cooling, sodium nitrite (3.31 g) dissolved in water (10 ml) was added dropwise thereto. The mixture was stirred at 0° C. for 1 hr. Potassium iodide (9.95 g) dissolved in water (20 ml) was added to the reaction mixture. The mixture was stirred at −4° C. for 2 hr. The mixture was adjusted to pH 11 or above with a 6N aqueous sodium hydroxide solution, and an aqueous thiosodium sulfate solution was added thereto. The mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried. The solvent was evaporated under reduced pressure to give a brown oil. The oil was purified by silica gel column chromatography (elution solvent: hexane) to give 3-iodo-2-methylbenzotrifluoride (6.28 g, yield 73%).

1. temperaturecooling
2. additionwas added dropwise
3. additionwas added to the reaction mixture
4. stirringThe mixture was stirred at −4° C. for 2 hr
5. extractionThe mixture was extracted with ethyl acetate
6. washThe extract was washed with saturated brine
7. customdried
8. customThe solvent was evaporated under reduced pressure
9. customto give a brown oil
10. customThe oil was purified by silica gel column chromatography (elution solvent: hexane)

ORD-Eintrag

ord-c61fc30ada0e4d4da524b8fd642907b4

Quelldatensatz

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07994196B2