Acetic Acid → 5-Bromo-2-phenoxyaniline

HRID 16176Notes

Reaction equation

HRID 16176 reaction equation
C(O)(=O)C.[Br:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:8]([N+:19]([O-])=O)[CH:7]=1>O.[Fe]>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:8]([NH2:19])[CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 161094494-Bromo-2-nitro-1-phenoxybenzene

Product 1

HCID 161094555-Bromo-2-phenoxyanilineYield 91.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Iron powder (3 g, 53.4 mmol) and acetic acid (10 mL) were added to a stirred suspension of 4-bromo-2-nitro-1-phenoxybenzene (3.1 g, 9.5 mmol) in water (25 mL) of 60° C. The reaction mixture was heated to 80° C. and stirred for 30 min. After cooling to room temperature the reaction mixture was filtered and extracted with toluene. The toluene solution was washed with water (3×) and brine, dried (Na2SO4) and evaporated to give the crude compound (2.3 g, 87%). Data: (m/z)=264+266 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. filtrationwas filtered
  3. extractionextracted with toluene
  4. washThe toluene solution was washed with water (3×) and brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-e541066c89164265be3270946fc57652
Source dataset
uspto-grants-2010_06
Patent number
US07737136B2

Reaction notes

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