4-Methoxybenzaldehyde → HCID 69373820, compound

HRID 861014Notes

Reaction equation

HRID 861014 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1>[NH4+].[Cl-]>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([CH:15]([C:14]2[CH:17]=[CH:18][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[OH:16])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 312444-MethoxybenzaldehydeHCID 693532,5-Dibromopyridine

Product 1

HCID 69373820HCID 69373820, compound

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2,5-dibromopyridine (1.0 eq.) in Tol (0.1M) at −78° C. was added n-BuUi (1.05 eq.). The mixture was stirred for 2 h at −78° C. then 4-methoxy-benzaldehyde (1.1 eq.) was added. The final mixture was warmed 0° C., poured in saturated aqueous NH4Cl and extracted with Et2O (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 9:1 to 3:2) and stirring in Hex:Et2O afforded the title compound as a white solid after filtration.

Workup

  1. extractionextracted with Et2O (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. stirringFlash chromatography (Hex:EtOAc; 9:1 to 3:2) and stirring in Hex

Sources & evidence

ORD record
ord-36e3040362cd4139bde0282a1ddc46dd
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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