Water → 5-Bromo-3-(trifluoromethyl)pyridin-2-amine

HRID 2174943Notes

Reaction equation

HRID 2174943 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[C:4]([NH2:9])=[N:5][CH:6]=[CH:7][CH:8]=1.[Br:12]Br.O>C(O)(=O)C>[Br:12][C:7]1[CH:8]=[C:3]([C:2]([F:1])([F:10])[F:11])[C:4]([NH2:9])=[N:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 27609202-Amino-3-(trifluoromethyl)pyridine

Product 1

HCID 205253835-Bromo-3-(trifluoromethyl)pyridin-2-amineYield 74%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-(trifluoromethyl)pyridin-2-amine (20 g, 123 mmol) was stirred in acetic acid (200 ml) at RT. Bromine (19.72 g, 123 mmol) was added drop wise with stirring. The reaction mixture was stirred for 2 h; followed by dilution with water. The product was extracted with ethyl acetate. Organic layer was washed with water, dried over sodium sulfate and concentrated to obtain the title product in 74% yield.

Workup

  1. stirringThe reaction mixture was stirred for 2 h
  2. extractionThe product was extracted with ethyl acetate
  3. washOrganic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-32f259d5fcfe46d494d060f16081d0a6
Source dataset
uspto-grants-2015_06
Patent number
US09062046B2

Reaction notes

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