3-Bromo-2-fluoropyridine → 3-Bromo-2-(tert-butoxy)pyridine

HRID 530653Notes

Reaction equation

HRID 530653 reaction equation
[Br:1][C:2]1[C:3](F)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:9][C:10]([CH3:13])([O-:12])[CH3:11].[K+]>O1CCCC1>[Br:1][C:2]1[C:3]([O:12][C:10]([CH3:13])([CH3:11])[CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 27627783-Bromo-2-fluoropyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 613737473-Bromo-2-(tert-butoxy)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-2-fluoropyridine (500 mg, 2.84 mmol) in anhydrous tetrahydrofuran (10 mL) under nitrogen was added potassium tert-butoxide (540 mg, 4.8 mmol) in portions over 30 minutes at 25° C., and stirring was continued for 4 hours at 25° C. The mixture was concentrated in vacuo and purified by silica gel flash chromatography eluting with dichloromethane/hexanes (50% to 100%) to give the title compound.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified by silica gel flash chromatography
  3. washeluting with dichloromethane/hexanes (50% to 100%)

Sources & evidence

ORD record
ord-76eca5031ba3425aa1d917895ac436f2
Source dataset
uspto-grants-2016_05
Patent number
US09353091B2

Reaction notes

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