N-bromobutanimide → 5-Bromo-3-(trifluoromethyl)pyridin-2-amine

HRID 445572Notes

Reaction equation

HRID 445572 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]N1C(=O)CCC1=O>CC#N>[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

4

Reactant 2

HCID 67184N-bromobutanimideHCID 27609202-Amino-3-(trifluoromethyl)pyridine

Product 1

HCID 205253835-Bromo-3-(trifluoromethyl)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-trifluoromethyl-pyridin-2-ylamine (Fluorochem Ltd., Derbyshire, United Kingdom, 5.37 g, 32.8 mmol) in 100 ml of dry CH3CN under argon were added N-bromosuccinimide (6.45 g, 36.2 mmol) in 4 equal portions over a period of 1 h at 0-5° C. The cooling bath was removed and stirring was continued for 3 h. The solvent was evaporated under vacuum, then the residue was dissolved in EtOAc and washed with water and brine. The organic layer was dried over Na2SO4 and evaporated to give the title compound as a orange oil. (M+H=239; 241).

Workup

  1. customThe cooling bath was removed
  2. customThe solvent was evaporated under vacuum
  3. dissolutionthe residue was dissolved in EtOAc
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-f6d7c9ae79934660842df9765f08cf0f
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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