Bromine → 2-Bromo-4-methoxy-6-nitroaniline

HRID 1935719Notes

Reaction equation

HRID 1935719 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.[Br:13]Br.C(=O)(O)[O-].[Na+]>ClCCl>[Br:13][C:8]1[CH:9]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[C:6]=1[NH2:7]

Participants

5

Reactant 3

HCID 24408BromineHCID 667934-Methoxy-2-nitroanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 219382042-Bromo-4-methoxy-6-nitroaniline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxy-2-nitroaniline (35 g) in dichloromethane (350 mL) was subsequently added dropwise bromine (12.9 mL) at −20° C. After stirring for 30 minutes at the same temperature, this was poured into ice water, adjusted to pH 7 to 8 with saturated sodium bicarbonate aqueous solution and then extracted with dichloromethane. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate). After concentration of the desired fraction, the resulting residue was crystallized from hexane and ethyl acetate and then collected by filtration to obtain the title compound as reddish orange crystals (29.6 g).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under a reduced pressure
  5. customThe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)
  6. customAfter concentration of the desired fraction, the resulting residue was crystallized from hexane and ethyl acetate
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-c90e5cfbd52e4409ab4c4299ab4b1c3d
Source dataset
uspto-grants-2002_05
Patent number
US06387938B1

Reaction notes

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