Hydrogen Bromide → 4-Chloro-3-nitrophenol

There were mixed 20 g of 4-chloro-3-nitroanisole, 67 ml of acetic acid and 83 ml of 47% (w/w) hydrobromic acid. Thereto was added 50 ml of acetic anhydride. The mixture was refluxed for 8.5 hours. After the completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was mixed with 300 ml of ethyl acetate and 500 ml of water. The resulting organic layer was separated, washed with a saturated aqueous sodium hydrogencarbonate solution, water and a saturated aqueous sodium chloride solution in this order, and then dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The resulting crystal was recrystallized from toluene to obtain 15.5 g (yield: 83.6%) of 4-chloro-3-nitrophenol having a melting point of 123.5°-125.5° C.

1. temperatureThe mixture was refluxed for 8.5 hours
2. customAfter the completion of the reaction
3. customthe solvent was removed by distillation under reduced pressure
4. additionThe residue was mixed with 300 ml of ethyl acetate and 500 ml of water
5. customThe resulting organic layer was separated
6. washwashed with a saturated aqueous sodium hydrogencarbonate solution, water
7. dry with materiala saturated aqueous sodium chloride solution in this order, and then dried with anhydrous magnesium sulfate
8. customThe solvent was removed by distillation under reduced pressure
9. customThe resulting crystal was recrystallized from toluene

ORD record

ord-5ea215b8ace24e9bb1f95c5eb15ded6e

Source dataset

uspto-grants-1990_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04954518