Dichloromethane → 2-BroMo-3,6-difluoropyridine

HRID 2046241Notes

Reaction equation

HRID 2046241 reaction equation
[Br:1]Br.[F:3][C:4]1[C:5](NN)=[N:6][C:7]([F:10])=[CH:8][CH:9]=1.C([O-])(O)=O.[Na+].C(Cl)Cl>C(Cl)(Cl)Cl>[Br:1][C:5]1[C:4]([F:3])=[CH:9][CH:8]=[C:7]([F:10])[N:6]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24408BromineHCID 516892Sodium BicarbonateHCID 53417183(3,6-difluoropyridin-2-yl)hydrazine

Product 1

HCID 729425092-BroMo-3,6-difluoropyridineYield 103.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

Bromine (0.30 mL, 6 mmol) was added dropwise to a stirred solution of (3,6-difluoro-pyridin-2-yl)-hydrazine (435 mg, 3 mmol) in CHCl3 (6 mL) at room temperature. The mixture was stirred at 60° C. for 1 hour. The mixture was cooled at 0° C. and a saturated solution of NaHCO3 was added dropwise. DCM was added, the organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo to yield 2-bromo-3,6-difluoro-pyridine (600 mg, 88% yield) as a dark oil.

Workup

  1. temperatureThe mixture was cooled at 0° C.
  2. customthe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-c809c41e966c4df988cac62950d11966
Source dataset
uspto-grants-2013_11
Patent number
US08592422B2

Reaction notes

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