1-(Benzyloxy)-2-bromo-4-nitrobenzene → 4-Benzyloxy-3-bromophenylamine

HRID 1157155Notes

Reaction equation

HRID 1157155 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=1[Br:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.O.Cl.[Fe]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([Br:18])[CH:11]=1

Participants

6

Reactant 1

HCID 220178401-(Benzyloxy)-2-bromo-4-nitrobenzene

Product 1

HCID 220177374-Benzyloxy-3-bromophenylamine

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidCatalystHCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-benzyloxy-2-bromo-4-nitrobenzene (50 mg, 0.16 mmol) in ethanol (5 mL) and H2O (0.5 mL) was added iron (134 mg, 2.43 mmol) and one drop of concentrated HCl. The mixture was refluxed for 6 hrs and filtrated. The filtrate was diluted with ethyl acetate, washed with saturated sodium bicarbonated solution, dried over sodium sulfate and concentrated to afford crude 4-amino-1-benzyloxy-2-bromobenzene.

Workup

  1. temperatureThe mixture was refluxed for 6 hrs
  2. filtrationfiltrated
  3. additionThe filtrate was diluted with ethyl acetate
  4. washwashed with saturated sodium bicarbonated solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-de2d28f143f94fd79d2e308c49dda941
Source dataset
uspto-grants-2010_10
Patent number
US07807672B2

Reaction notes

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