Bromine → HCID 18451499, compound

HRID 1270741Notes

Reaction equation

HRID 1270741 reaction equation
[Cl:1][C:2]1[C:8]([F:9])=[CH:7][C:6]([CH3:10])=[C:5]([F:11])[C:3]=1[NH2:4].[Br:12]Br>CO>[Cl:1][C:2]1[C:8]([F:9])=[C:7]([Br:12])[C:6]([CH3:10])=[C:5]([F:11])[C:3]=1[NH2:4]

Participants

4

Reactant 2

HCID 24408BromineHCID 18451509HCID 18451509, compound

Product 1

HCID 18451499HCID 18451499, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-chloro-5-methyl-3,6-difluoroaniline (5.0 g, 28 mmol) in anhydrous methanol (25 mL) is treated with elemental bromine (5.0 g, 3,1 mmol) at room temperature. After stirring for 12 hours, most of the solvent is removed by rotary evaporator and the residue partitioned between EtOAc (250 mL) and water (250 mL). The organic phase is washed with brine (150 mL), dried (MgSO4) and concentrated by rotary evaporator. The crude product is purified using flash chromatography (7% EtOAc/hexanes) to give 2-chloro-4-bromo-5-methyl-3,6-difluoroaniline as a tan solid.

Workup

  1. customis removed by rotary evaporator
  2. customthe residue partitioned between EtOAc (250 mL) and water (250 mL)
  3. washThe organic phase is washed with brine (150 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated by rotary evaporator
  6. customThe crude product is purified

Sources & evidence

ORD record
ord-f0e5510f5c1641adbc0b47dae725ff20
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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