Sulfuric Acid → 3-Bromo-2-(difluoromethoxy)aniline

HRID 429594Notes

Reaction equation

HRID 429594 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[C:8]([O:16][CH:17]([F:19])[F:18])=[C:9]([N+:13]([O-])=O)[CH:10]=[CH:11][CH:12]=1>[Fe].O>[Br:6][C:7]1[C:8]([O:16][CH:17]([F:18])[F:19])=[C:9]([CH:10]=[CH:11][CH:12]=1)[NH2:13]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 158867431-Bromo-2-(difluoromethoxy)-3-nitrobenzene

Product 1

HCID 158867443-Bromo-2-(difluoromethoxy)anilineYield 65.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent2×

Procedure

Into a 100-ml four-necked flask provided with a reflux condenser, a stirrer and a thermometer were fed 0.95 g (17.0 mmol) of an iron powder, 0.11 g (1.0 mmol) of 98% sulfuric acid, 15 ml of water and 1.62 g (6.0 mmol) of 3-bromo-2-difluoromethoxynitrobenzene. The mixture was heated on an oil bath and refluxed for 2 hours. After the completion of a reaction, azeotropic distillation was conducted while 220 ml of water was added gradually. The distillate was subjected to extraction two times each using 100 ml of ether. The ether layer was dried over anhydrous sodium sulfate and then subjected to distillation. The residue was distilled under vacuum to obtain 0.94 g of 3-bromo-2-difluoromethoxyaniline (yield: 65.4%, purity: 98.5%).

Workup

  1. customInto a 100-ml four-necked flask provided with a reflux condenser, a stirrer
  2. temperatureThe mixture was heated on an oil bath
  3. temperaturerefluxed for 2 hours
  4. customAfter the completion of a reaction, azeotropic distillation
  5. additionwas added gradually
  6. extractionThe distillate was subjected to extraction two times each using 100 ml of ether
  7. dry with materialThe ether layer was dried over anhydrous sodium sulfate
  8. distillationsubjected to distillation
  9. distillationThe residue was distilled under vacuum

Sources & evidence

ORD record
ord-84bc3130f2424348ad9cf32c5f87d500
Source dataset
uspto-grants-2001_11
Patent number
US06316658B1

Reaction notes

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