Pyridine → 2-Bromo-4-chloro-6-methylbenzenamine

HRID 855239Notes

Reaction equation

HRID 855239 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.N1C=CC=CC=1.[Br:16]Br>C(Cl)Cl>[Br:16][C:7]1[CH:8]=[C:2]([Cl:1])[CH:3]=[C:4]([CH3:9])[C:5]=1[NH2:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 72514-Chloro-2-toluidineHCID 24408Bromine

Product 1

HCID 205437542-Bromo-4-chloro-6-methylbenzenamineYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.83 g (20 mmol) of 4-chloro-2-methyl aniline and 1.74 g (22 mmol) of pyridine were dissolved in 20 ml DCM. 3.20 g (20 mmol) of bromine were added dropwise under cooling. The reaction mixture was stirred for 2 h at rt. The solvent was removed and the residue was dissolved in diethyl ether. The organic layer was washed with water, dried over sodium sulfate, filtered and the solvent was evaporated. The crude product was purified by column chromatography (silica gel; diethyl ether/heptane 1:1) to yield 3.91 g (89%) of 2-bromo-4-chloro-6-methyl aniline as a light green solid. 1H NMR (CDCl3, 300 MHz): δ 7.30 (s, 1H), 6.99 (s, 1H), 4.04 (br s, 2H), 2.19 (s, 3H).

Workup

  1. temperatureunder cooling
  2. customThe solvent was removed
  3. dissolutionthe residue was dissolved in diethyl ether
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe crude product was purified by column chromatography (silica gel; diethyl ether/heptane 1:1)

Sources & evidence

ORD record
ord-473342d8ef434eebbe2e8436db4fcc66
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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