Water → HCID 56777236, compound

HRID 2036744Notes

Reaction equation

HRID 2036744 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Br:15])[CH:12]=[CH:11][C:10]=1[N+:16]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].O>C(O)C.[Fe]>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Br:15])[CH:12]=[CH:11][C:10]=1[NH2:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 67085084HCID 67085084, compound

Product 1

HCID 56777236HCID 56777236, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-(benzyloxy)-4-bromo-1-nitrobenzene (14.1 g, 45.8 mmol), iron powder (12.8 g, 229.12 mmol) and ammonium chloride (2.9 g, 55.0 mmol) was taken up in ethanol (60 mL) and water (30 mL) and heated at 90° C. for 3 h. After cooling to ambient temperature, the reaction mixture was filtered through a celite bed and the filtrate concentrated in vacuo. The aqueous residue was extracted with dichloromethane and the organic layer washed with brine, dried over sodium sulfate and concentrated in vacuo to give 2-(benzyloxy)-4-bromoaniline (12.6 g, 99%) as a purple oil: 1H NMR (CDCl3, 300 MHz) δ 7.31-7.46 (m, 5H), 6.98 (d, J=2.1 Hz, 1H), 6.92 (dd, J=8.4, 2.1 Hz, 1H), 6.60 (d, J=8.4 Hz, 1H), 5.05 (s, 2H), 3.81 (br s, 2H).

Workup

  1. filtrationthe reaction mixture was filtered through a celite bed
  2. concentrationthe filtrate concentrated in vacuo
  3. extractionThe aqueous residue was extracted with dichloromethane
  4. washthe organic layer washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60c0a045d2d44a40a0056815b7df176e
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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