Acetic Acid → 2-Bromo-6-nitrophenol

HRID 429592Notes

Reaction equation

HRID 429592 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(O)(=O)C.[N+:13]([O-])([OH:15])=[O:14]>O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:13]([O-:15])=[O:14])[C:3]=1[OH:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 72442-Bromophenol

Product 1

HCID 135454532-Bromo-6-nitrophenolYield 34.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

51.9 g (0.3 mol) of 2-bromophenol and 300 ml of acetic acid were fed into a 1-liter four-necked flask provided with a reflux condenser, a stirrer and a thermometer. Thereto was dropwise added 29.7 g (0.33 mol) of 70% nitric acid at a temperature of 15° C. or below, with ice-cooling. The reaction mixture was stirred at a temperature of 10° C. or below for 1 hour and poured into 600 ml of water. The mixture was subjected to extraction with 400 ml of ether. The ether layer was washed with 150 ml of water. The ether layer was subjected to distillation. The residue was transferred into a 1-liter flask provided with a stirrer and a distillation apparatus. Azeotropic distillation was conducted while water was added gradually. The amount of water required for azeotropic distillation was 2,100 ml. The distillate obtained was subjected to extraction two times using 500 ml of ether. The ether layer was dried over anhydrous sodium sulfate and subjected to distillation to remove ether. The resulting crude product was mixed with 10 ml of ethanol. The mixture was heated and then allowed to cool. The formed crystals were collected by filtration and then dried to obtain 22.3 g of 2-bromo-6-nitrophenol (yield: 34.1%, purity: 99.6%).

Workup

  1. customprovided with a reflux condenser, a stirrer
  2. customat a temperature of 15° C. or below
  3. temperaturewith ice-cooling
  4. extractionThe mixture was subjected to extraction with 400 ml of ether
  5. washThe ether layer was washed with 150 ml of water
  6. distillationThe ether layer was subjected to distillation
  7. customThe residue was transferred into a 1-liter flask
  8. customprovided with a stirrer
  9. distillationAzeotropic distillation
  10. additionwas added gradually
  11. distillationThe amount of water required for azeotropic distillation
  12. customThe distillate obtained
  13. extractionwas subjected to extraction two times
  14. dry with materialThe ether layer was dried over anhydrous sodium sulfate
  15. distillationsubjected to distillation
  16. customto remove ether
  17. additionThe resulting crude product was mixed with 10 ml of ethanol
  18. temperatureThe mixture was heated
  19. temperatureto cool
  20. filtrationThe formed crystals were collected by filtration
  21. customdried

Sources & evidence

ORD record
ord-9e504c340ea24ca9878d091ed0e8d83f
Source dataset
uspto-grants-2001_11
Patent number
US06316658B1

Reaction notes

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