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

HRID 1396574Notes

Reaction equation

HRID 1396574 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:12]Br>C(Cl)(Cl)Cl.CC(O)=O>[Br:12][C:5]1[CH:6]=[C:7]([C:8]([F:9])([F:11])[F:10])[C:2]([NH2:1])=[N:3][CH:4]=1

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent2×

Procedure

2-amino-3-trifluoromethylpyridine (0.980 g, 5.92 mmol) is dissolved in CHCl3 (7 ml) and AcOH (5 ml). The reaction mixture is cooled to 0-10° C. (ice-bath) and bromine (0.424 ml, 8.3 mmol) dissolved in CHCl3 is slowly added drop wise. The reaction mixture is stirred at this temperature for 1 hour then allowed to warm room temperature. The solvents are removed in vacuo and the residue is dissolved in EtOAc washing with saturated NaHCO3. The organic portion is dried over MgSO4, filtered and concentrated to afford the title compound.

Workup

  1. customThe solvents are removed in vacuo
  2. dissolutionthe residue is dissolved in EtOAc washing with saturated NaHCO3
  3. dry with materialThe organic portion is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a262b0896fb84ebaa5d902e6f074e143
Source dataset
uspto-grants-2014_12
Patent number
US08901134B2

Reaction notes

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