Ethanol → 3-(3-Bromo-phenoxymethyl)-phenylamine

HRID 607219Notes

Reaction equation

HRID 607219 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[CH:13]=2)[CH:5]=1)([O-])=O.[Cl-].[NH4+].O.C(O)C>O1CCCC1.[Fe]>[Br:18][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[O:11][CH2:10][C:6]1[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 283695411-Nitro-3-(3-bromo-phenoxymethyl)-benzene

Product 1

HCID 201129593-(3-Bromo-phenoxymethyl)-phenylamineYield 97%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Example 104A (1.64 g, 5.32 mmol), iron powder (1.49 g, 26.62 mmol) and ammonium chloride (430 mg, 7.98 mmol) in a mixture of tetrahydrofuran (20 mL), water (6 mL) and ethanol (20 mL) was heated to reflux for 3 hours. The mixture was cooled to room temperature, filtered through a pad of celite, which was washed with ethanol and the resultant filtrate concentrated under vacuum. The material was then dissolved in water (50 mL) and extracted with ethyl acetate (50 mL), the organic layer dried and concentrated under vacuum to provide the title compound as a yellow oil (1.43 g, 97%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. filtrationfiltered through a pad of celite, which
  4. washwas washed with ethanol
  5. concentrationthe resultant filtrate concentrated under vacuum
  6. dissolutionThe material was then dissolved in water (50 mL)
  7. extractionextracted with ethyl acetate (50 mL)
  8. customthe organic layer dried
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cba2877cacb1487c83615460cf0ad156
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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