Bromine → 3-Bromo-6-(trifluoromethyl)pyridin-2-amine

HRID 451465

Reaction equation

HRID 451465 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[N:8]=[C:7]([NH2:9])[CH:6]=[CH:5][CH:4]=1.[Br:12]Br>ClCCl>[Br:12][C:6]1[C:7]([NH2:9])=[N:8][C:3]([C:2]([F:1])([F:10])[F:11])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 8210242-Amino-6-(trifluoromethyl)pyridine

Product 1

HCID 547588353-Bromo-6-(trifluoromethyl)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-(trifluoromethyl)pyridin-2-amine (200 mg, 1.23 mmol) in dichlormethane (2.47 mL) was cooled to 0° C. and bromine (197 mg, 63.4 μL, 1.23 mmol) was slowly added within 30 minutes. After 25 hours at 0° C. the reaction mixture was extracted with saturated Na2S2O3 solution, water and brine, dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography over silica gel using CH2Cl2/MeOH (with 10% ammonia) as eluent. The title compound was obtained as a white solid (711 mg, 24%).

Workup

  1. extractionAfter 25 hours at 0° C. the reaction mixture was extracted with saturated Na2S2O3 solution, water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-f55ec016212748739785ce7fd3b023d5
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Linked notes

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