2,6-Dibromopyridine → HCID 86602990, compound

HRID 2099574Notes

Reaction equation

HRID 2099574 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[Li]CCCC.[Br:14][C:15]1[N:20]=[C:19]([CH:21]=[O:22])[CH:18]=[CH:17][CH:16]=1>C1COCC1>[Br:8][C:4]1[N:3]=[C:2]([CH:21]([C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([Br:14])[N:20]=2)[OH:22])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 122742,6-DibromopyridineHCID 27570096-Bromopyridine-2-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 86602990HCID 86602990, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 2,6-dibromopyridine (4.72 g, 19.93 mmol) in THF (100 mL) at −78° C. was added n-BuLi (8.8 mL, 2.5 M, 22 mmol) and stirred for 20 min. 6-Bromo-2-pyridinecarboxaldehyde (3.71 g, 19.93 mmol) was added. The mixture was stirred at 0° C. for 2 h. The reaction was quenched with ice and extracted with CH2Cl2. The combined organic layer was dried, filtered, and concentrated to give a solid. The solid was purified by silica gel chromatography (15% EtOAc in hexane) to give bis(6-bromopyridin-2-yl)methanol. LRMS m/z (M+H) Calcd: 345.0, found: 344.9.

Workup

  1. stirringThe mixture was stirred at 0° C. for 2 h
  2. customThe reaction was quenched with ice
  3. extractionextracted with CH2Cl2
  4. customThe combined organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a solid
  8. customThe solid was purified by silica gel chromatography (15% EtOAc in hexane)

Sources & evidence

ORD record
ord-328cd4527f534fda84cc417ddd731041
Source dataset
uspto-grants-2009_08
Patent number
US07569589B2

Reaction notes

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