Pyridine → 6-Bromo-2-(bromomethyl)-3-fluoropyridine

HRID 1258557Notes

Reaction equation

HRID 1258557 reaction equation
S(Br)([Br:3])=O.[Br:5][C:6]1[N:11]=[C:10]([CH2:12]O)[C:9]([F:14])=[CH:8][CH:7]=1.N1C=CC=CC=1>C(Cl)Cl>[Br:5][C:6]1[N:11]=[C:10]([CH2:12][Br:3])[C:9]([F:14])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 68176Thionyl bromideHCID 53485567(6-Bromo-3-fluoropyridin-2-yl)methanol

Product 1

HCID 866422856-Bromo-2-(bromomethyl)-3-fluoropyridineYield 95.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution thionyl bromide (2.44 g, 11.78 mmol, 1.05 eq.) in 50 ml dry DCM, cooled to 5° C., was added dropwise a solution of (6-bromo-3-fluoropyridin-2-yl)methanol (2.54 g, 11.22 mmol, 1 eq.) and pyridine (0.931 g, 11.78 mmol, 1.05 eq.) in 15 ml dry DCM. On complete addition, the cooling bath was removed, the reaction warmed to room temperature and stirred 1.5 hr. 150 ml of water and 150 ml of DCM were added and stirring allowed for 2 mins. The organic layer was separated, dried of MgSO4 and concentrated. The residue was purified by chromatography on silica gel to give 6-bromo-2-(bromomethyl)-3-fluoropyridine (2.89 g, 87% yield) as a white solid.

Workup

  1. additionOn complete addition
  2. customthe cooling bath was removed
  3. addition150 ml of water and 150 ml of DCM were added
  4. stirringstirring
  5. waitallowed for 2 mins
  6. customThe organic layer was separated
  7. dry with materialdried of MgSO4
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-b3399bd5cf3e406985a575a82f1604e6
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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