2-Bromopyridine → HCID 13058732, compound

HRID 711391Notes

Reaction equation

HRID 711391 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9](Cl)(Cl)Cl)=[CH:4][CH:3]=1.Br[C:14]1[CH:19]=[CH:18][CH:17]=C[N:15]=1>C(N)=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:17]=[CH:18][CH:19]=[CH:14][N:15]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 79732-BromopyridineHCID 21224760HCID 21224760, compound

Product 1

HCID 13058732HCID 13058732, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 713FormamideSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A solution of (4-bromophenyl)(trichloromethyl)sulfane (0.25 g, 0.816 mmol) in 12 mL of formamide was degassed with nitrogen and treated with 2-bromopyridine (0.078 ml, 0.816 mmol). The reaction solution was heated at 75° C. overnight. Then it was cooled to room temperature and diluted with water, extracted with DCM, dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography on silica gel, eluted with 1-5% of EtOAc in 20% DCM/heptanes (v/v), affording 0.14 g (65% yield) of 2-((4-bromophenyl)thio)pyridine.

Workup

  1. temperatureThen it was cooled to room temperature
  2. extractionextracted with DCM
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography on silica gel
  7. washeluted with 1-5% of EtOAc in 20% DCM/heptanes (v/v)

Sources & evidence

ORD record
ord-074fbe53de2f44449cd64b3e25233c2d
Source dataset
uspto-grants-2015_11
Patent number
US09181270B2

Reaction notes

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