Iodine → Benzene, 2-fluoro-1-iodo-4-methyl-

Temperature

-72 °C

Under dry nitrogen, a solution prepared by dissolving 4-bromo-3-fluorotoluene (10 g) in THF (50 mL) was cooled to −72° C. Then, a 1.6 mol/L n-butyl lithium hexane solution (35 mL) was added at −72° C. to the solution such a rate that the inside temperature was not more than −65° C., followed by further stirring at −72° C. for 1 hour. A solution prepared by dissolving iodine (14.8 g) in THF (30 mL) was added at −72° C. to the resultant mixture such a rate that the inside temperature was not more than −60° C., and the temperature was slowly increased to room temperature. Then, a saturated aqueous ammonium chloride solution and hexane were added at room temperature to separate an organic layer, and the organic layer was washed with a 10% aqueous sodium sulfite solution two times and saturated brine in that order, and then dried with sodium sulfate. The sodium sulfate was filtered off, and the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to yield 13.0 g of 3-fluoro-4-iodotoluene as a yellow liquid.

1. customUnder dry nitrogen, a solution prepared
2. customwas not more than −65° C.
3. customA solution prepared
4. customwas not more than −60° C.
5. temperaturethe temperature was slowly increased to room temperature
6. customto separate an organic layer
7. washthe organic layer was washed with a 10% aqueous sodium sulfite solution two times and saturated brine in that order
8. dry with materialdried with sodium sulfate
9. filtrationThe sodium sulfate was filtered off
10. distillationthe organic solvent was distilled off under reduced pressure
11. customThe residue was purified by silica gel column chromatography

ORD record

ord-844e44ec9a7343929a9fe874d8ba0d08

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916718B2