2-Bromoanisole → 4-Bromo-3-methoxyaniline

HRID 1006170Notes

Reaction equation

HRID 1006170 reaction equation
[Cl-].[NH4+:2].[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH3:11]>O.CO.[Fe]>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:2])=[CH:6][C:5]=1[O:10][CH3:11]

Participants

6

Reactant 2

HCID 113582-BromoanisoleHCID 25517Ammonium Chloride

Product 1

HCID 70182544-Bromo-3-methoxyanilineYield 99.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A suspension of iron powder (40.8 g, 0.730 mol), ammonium chloride (64.7 g, 1.21 mol) and 2-bromoanisole (50 g, 0.215 mol) in water (1.5 L) and MeOH (1 L) was stirred overnight at 75° C. The solid was filtered off and the liquid was diluted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered and the solvents were evaporated under vacuum. 43.1 g of the title compound were obtained. Brown solid, ISP-MS: m/e=203.1 ([M+H]+).

Workup

  1. filtrationThe solid was filtered off
  2. additionthe liquid was diluted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvents were evaporated under vacuum

Sources & evidence

ORD record
ord-cda5befb9e4f4d74a5e6f832cf269978
Source dataset
uspto-grants-2004_09
Patent number
US06787558B2

Reaction notes

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