2-Methoxyaniline → 4-Bromo-2-methoxyaniline

HRID 2384896Notes

Reaction equation

HRID 2384896 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11]>C(Cl)Cl>[Br:1][C:9]1[CH:8]=[CH:7][C:6]([NH2:11])=[C:5]([O:4][CH3:3])[CH:10]=1

Participants

4

Reactant 2

HCID 70002-MethoxyanilineHCID 24408Bromine

Product 1

HCID 4592574-Bromo-2-methoxyanilineYield 59.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add dropwise a solution of bromine (0.83 mL, 16.2 mmol) in CH2Cl2 (130 mL) to a solution of 2-methoxy-phenylamine (2.0 g, 16.2 mmol) in dichloromethane (100 mL) at 0° C. over a period of 45 min. Stir the mixture at 0° C. to RT overnight. Wash the mixture with water, dry over Na2SO4, filter, and concentrate. Purify the crude material by flash chromatography eluting with 10% EtOAc/hexane to give 1.95 g (59%) of the title compound. GC m/z (81Br) 203 [M+].

Workup

  1. washWash the mixture with water
  2. dry with materialdry over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the crude material by flash chromatography
  6. washeluting with 10% EtOAc/hexane

Sources & evidence

ORD record
ord-414c9cb5c90545c48a9987d48919ca6f
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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