Ammonium Chloride → 4-[2-Amino-4-(3-bromo-benzyloxy)-phenoxy]-phenol

HRID 607303Notes

Reaction equation

HRID 607303 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][O:6][C:7]1[CH:20]=[CH:19][C:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[C:9]([N+:21]([O-])=O)[CH:8]=1.[Cl-].[NH4+]>O.C(O)C.[Fe]>[NH2:21][C:9]1[CH:8]=[C:7]([O:6][CH2:5][C:4]2[CH:24]=[CH:25][CH:26]=[C:2]([Br:1])[CH:3]=2)[CH:20]=[CH:19][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 668085764-[4-(3-Bromo-benzyloxy)-2-nitro-phenoxy]-phenol

Product 1

HCID 668084754-[2-Amino-4-(3-bromo-benzyloxy)-phenoxy]-phenolYield 76.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of the product from Example 218A (384.6 mg, 0.924 mmol), iron powder (317.4 mg, 5.683 mmol), and ammonium chloride (323.7 mg, 6.052 mmol) in water (3 mL) and ethanol (6 mL) was heated at 70° under a nitrogen atmosphere for 1 hour. The reaction was cooled to room temperature and vacuum filtered, washing the residue with methanol. The filtrate was concentrated under vacuum and azeotroped with toluene (50 mL). The residue was purified by silica gel flash chromatography using a gradient of 7% to 10% ethyl acetate/methylene chloride as eluent to provide the title compound as a beige solid (272 mg, 0.704 mmol, 76%).

Workup

  1. temperaturewas heated at 70° under a nitrogen atmosphere for 1 hour
  2. filtrationvacuum filtered
  3. washwashing the residue with methanol
  4. concentrationThe filtrate was concentrated under vacuum
  5. customazeotroped with toluene (50 mL)
  6. customThe residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-ed85022234de4f0cb293b4ace039aec4
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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