Methanol → HCID 21708319, compound

6.54 g (22.1 mmol) of 3-bromo-4-chloro-5-(1-fluoropropyl)-1-nitrobenzene was dissolved in a solvent mixture comprising 30 ml of methanol and 90 ml of acetonitrile, followed by the addition of 120 ml of a 20% solution of titanium trichloride in diluted hydrochloric acid under a nitrogen stream under cooling with ice. The obtained mixture was stirred at room temperature for 3 hours and then poured into water. The resulting mixture was extracted with ethyl acetate. The ethyl acetate phase was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated brine successively, dried and distilled to remove the solvent. The residue was purified by silica gel column chromatography to give 5.04 g of the title compound (yield: 86%).

1. temperatureunder cooling with ice
2. extractionThe resulting mixture was extracted with ethyl acetate
3. washThe ethyl acetate phase was washed with a saturated aqueous solution of sodium hydrogen carbonate
4. dry with materiala saturated brine successively, dried
5. distillationdistilled
6. customto remove the solvent
7. customThe residue was purified by silica gel column chromatography

ORD record

ord-352cec8ee0f34c45bda93b443c741a8d

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05849912