Hydrochloric Acid → 1-Iodo-4-(trifluoromethoxy)benzene

Temperature

-5 °C

4-Trifluoromethoxyaniline (29.0 g.) was added at 0° C. to concentrated hydrochloric acid (160 mls.) and the thick white suspension so obtained was cooled to -5° C. The suspension was diazotised by adding a solution of sodium nitrite (13.0 g.) in water (20 ml.) over 20 minutes, keeping the temperature below 0° C. After 2 hours at 0° C., the suspension was added portionwise to a solution of potassium iodide (40 g.) and iodine (60 g.) in water (260 ml.) at 10° C. and the solution was allowed to stand at room temperature for 1 hour. The dark solution so obtained was extracted with diethyl ether three times, and the combined ether extracts were washed sequentially with sodium sulphite, water and brine, and on evaporation gave a golden oil which was distilled under water pump pressure to give 4-trifluoromethoxyiodobenzene as a pale pink liquid, b.p. 107°-8° C.

1. customthe thick white suspension so obtained
2. customthe temperature below 0° C
3. waitto stand at room temperature for 1 hour
4. customThe dark solution so obtained
5. extractionwas extracted with diethyl ether three times
6. washthe combined ether extracts were washed sequentially with sodium sulphite, water and brine
7. customon evaporation
8. customgave a golden oil which
9. distillationwas distilled under water

ORD record

ord-f77aa6af77874f2da546aacc7c986f7a

Source dataset

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04925863