Aniline → 4-Bromo-2-methoxyaniline

HRID 279991

Reaction equation

HRID 279991 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].[Br:10]C1C(=O)C(Br)=CC(Br)(Br)C=1.NC1C=CC=CC=1>C(Cl)Cl>[Br:10][C:8]1[CH:7]=[CH:6][C:4]([NH2:5])=[C:3]([O:2][CH3:1])[CH:9]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 70002-MethoxyanilineHCID 884332,4,4,6-Tetrabromocyclohexa-2,5-dienone

Product 1

HCID 4592574-Bromo-2-methoxyaniline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methoxyaniline (o-anisidine) (15 g, 0.122 mol) was brominated with 2,4,4,6-tetrabromo-2,5-cyclohexadienone (50 g, 0.122 mol) by dissolving the aniline in 250 ml of methylene chloride, chilling the solution to -10°, and slowly adding and brominating agent, keeping the temperature below -5°. The reaction was allowed to warm at room temperature, and then washed with 2N sodium hydroxide (2×75 ml), then washed with water (2×25 ml), dried over magnesium sulfate, and evaporated to dryness. The product was purified on a silica gel column, eluted with methylene chloride giving 23.68 g (96%) of the title compound, mp 56.5°-58° (petroleum ether). Anal. Calcd for C7H8BrNO: C, 41.61; H, 3.99; Br, 39.55; N, 6.93. Found: C, 41.59; H, 3.99; Br, 39.49; N, 6.92.

Workup

  1. temperaturechilling the solution to -10°
  2. additionslowly adding
  3. customthe temperature below -5°
  4. washwashed with 2N sodium hydroxide (2×75 ml)
  5. washwashed with water (2×25 ml)
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness
  8. customThe product was purified on a silica gel column
  9. washeluted with methylene chloride giving 23.68 g (96%) of the title compound, mp 56.5°-58° (petroleum ether)

Sources & evidence

ORD record
ord-2a6ee27e7334490a8218b93befa21e37
Source dataset
uspto-grants-1986_05
Patent number
US04587341

Linked notes

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