Sodium Sulfite → 2-Bromo-4-chloro-5-methoxyaniline

HRID 705369Notes

Reaction equation

HRID 705369 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[O:9][CH3:10].[Br:11]N1C(=O)CCC1=O.[O-]S([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:11][C:7]1[CH:8]=[C:2]([Cl:1])[C:3]([O:9][CH3:10])=[CH:4][C:5]=1[NH2:6]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 67184N-bromobutanimideHCID 131036924-Chloro-3-methoxyaniline

Product 1

HCID 147747832-Bromo-4-chloro-5-methoxyanilineYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 4-chloro-3-methoxyaniline (1.0 equivalent) dissolved in CH2Cl2 (15 volumes) at 5° C. was treated portion wise with N-bromosuccinimide (1.03 equivalents), warmed to 20° C. and mixed for 5 minutes. A 5% aqueous Na2SO3 solution (10 volumes) was added and the mixture was stirred for 10 minutes. The layers were separated and the organic layer was washed with water and saturated brine, dried (Na2SO4), filtered and concentrated. The resulting solid was triturated with a minimal volume of heptane and the solid was collected by filtration and dried to constant mass (80% yield).

Workup

  1. additionmixed for 5 minutes
  2. customThe layers were separated
  3. washthe organic layer was washed with water and saturated brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting solid was triturated with a minimal volume of heptane
  8. filtrationthe solid was collected by filtration
  9. customdried to constant mass (80% yield)

Sources & evidence

ORD record
ord-58383cd619f7474585f0ed824f65dcf6
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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