Bromine → 4-Bromo-5-chloro-2-methoxyaniline

HRID 2260925Notes

Reaction equation

HRID 2260925 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:5]=[C:6]([NH2:12])[C:7](=[CH:10][CH:11]=1)[O:8][CH3:9]>ClCCl>[Cl:3][C:4]1[C:11]([Br:1])=[CH:10][C:7]([O:8][CH3:9])=[C:6]([NH2:12])[CH:5]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 667635-Chloro-2-methoxyaniline

Product 1

HCID 229976674-Bromo-5-chloro-2-methoxyanilineYield 33.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromine (26.4 g) was added to a solution of 4-chloro-o-anisidine (23.55 g) in dichloromethane (400 mL) at room temperature. The resulting mixture was stirred for 10 hours and quenched with NaOH. The organic layer was washed with brine, dried over MgSO4, and concentrated. Purification by flash chromatography over silica gel (elution with 10% ethyl acetate in hexanes) gave 11.8 g (33%) of the desired 4-chloro-5-bromo-2-aminoanisole. 1H NMR (300 MHz, CDC13) d 6.94 (s, 1 H), 6.78 (s, 1 H), 3.83 (s, 3 H).

Workup

  1. customquenched with NaOH
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customPurification by flash chromatography over silica gel (elution with 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-d1d00990fc8449d6b45eb873db2047ff
Source dataset
uspto-grants-2010_12
Patent number
US07846671B2

Reaction notes

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