2-Bromo-3-nitroanisole → 2-Bromo-3-methoxyaniline

HRID 2178673Notes

Reaction equation

HRID 2178673 reaction equation
[Br:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH3:12]>C(O)C.Cl.[Fe]>[Br:1][C:2]1[C:3]([O:11][CH3:12])=[CH:4][CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

5

Reactant 1

HCID 177502992-Bromo-3-nitroanisole

Product 1

HCID 109105752-Bromo-3-methoxyaniline

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

Iron (1.94 g, 34 mmol) was added to a solution of 2-bromo-1-methoxy-3-nitrobenzene (2.50 g, 10.77 mmol) in ethanol (18 mL) and concentrated hydrochloric acid (1 mL), and the reaction was heated at reflux for 1.5 hours. The mixture was cooled to room temperature, filtered through Celite and concentrated in vacuo to afford the title compound as a solid. Yield: 2.57 g, 10.77 mmol, 100%. LCMS m/z 202.1 (M+1). 1H NMR (400 MHz, CD3OD) δ 3.77 (s, 3H), 6.30 (d, J=8.0 Hz, 1H), 6.43 (d, J=8.0 Hz, 1H), 6.98 (dd, J=8.0, 8.0 Hz, 1H).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 1.5 hours
  3. filtrationfiltered through Celite
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-627fc7bde65a455bb33f43e45435ed2a
Source dataset
uspto-grants-2015_06
Patent number
US09067934B2

Reaction notes

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