Acetic Acid → 3-Chloro-4-(3-chlorophenoxy)aniline

HRID 38242

Reaction equation

HRID 38242 reaction equation
C(O)(=O)C.[Cl:5][C:6]1[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[CH:8][C:7]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=1>O.CCO.[Fe]>[Cl:5][C:6]1[CH:11]=[C:10]([CH:9]=[CH:8][C:7]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=1)[NH2:12]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 2752072-Chloro-1-(3-chlorophenoxy)-4-nitrobenzene

Product 1

HCID 176055343-Chloro-4-(3-chlorophenoxy)anilineYield 100%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

According to Scheme 3 Step 2: A suspension of iron (5.07 mmol, 283 mg), acetic acid (1.22 mmol, 70 μL) and of 2-chloro-1-(3-chlorophenoxy)-4-nitrobenzene (1.02 mmol, 288 mg) in water/EtOH (1:1, 8 mL) was stirred at 80° C. for 30 minutes. After evaporation of EtOH, the aqueous phase was basified with a saturated solution of NaHCO3 and was extracted with AcOEt. The organic phase was washed with brine, was dried over MgSO4, was filtered and was concentrated under reduced pressure to yield 3-chloro-4-(3-chlorophenoxy)aniline (1.02 mmol, 258 mg, 100%) as a solid. The product was used without further purification.

Workup

  1. customAfter evaporation of EtOH
  2. extractionwas extracted with AcOEt
  3. washThe organic phase was washed with brine
  4. dry with materialwas dried over MgSO4
  5. filtrationwas filtered
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-077c9c4ea8274fb796a20617fa6ba2d7
Source dataset
uspto-grants-2013_09
Patent number
US08524726B2

Linked notes

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