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

HRID 558581Notes

Reaction equation

HRID 558581 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.C1C(=O)N([Br:19])C(=O)C1.C([O-])(O)=O.[Na+]>C(#N)C>[Br:19][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 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 27609202-Amino-3-(trifluoromethyl)pyridine

Product 1

HCID 205253835-Bromo-3-(trifluoromethyl)pyridin-2-amineYield 98.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 3-trifluoromethyl-pyridin-2-ylamine (16.21 g, 100 mmol) in acetonitrile (300 mL) at 5° C. was added NBS (17.8 g, 100 mmol) and the mixture was stirred at 23° C. for 1 h. Poured onto ice and sat. NaHCO3 soln., extracted with EtOAc, washed with brine, dried over Na2SO4. Removal of the solvent in vacuum left a yellow solid. Silica gel & cotton wool column filtration with DCM gave the product as a yellow solid (23.71 g, 98%). MS (ISP) 240.1 [(M+H)+].

Workup

  1. extraction, extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customRemoval of the solvent in vacuum
  5. waitleft a yellow solid
  6. filtrationSilica gel & cotton wool column filtration with DCM

Sources & evidence

ORD record
ord-b56b5e2aaeb140e2a0de755bd0ffe61f
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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