Dimethylformamide → 2,3-Dichloro-4-(chloromethyl)pyridine

HRID 1355528Notes

Reaction equation

HRID 1355528 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([CH2:9]O)[CH:5]=[CH:4][N:3]=1.CN(C=O)C.O=P(Cl)(Cl)[Cl:18]>N#N>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([CH2:9][Cl:18])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 18506935(2,3-Dichloro-4-pyridinyl)methanol

Product 1

HCID 185068502,3-Dichloro-4-(chloromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 947NitrogenSolvent

Procedure

(2,3-Dichloro-pyridin-4-yl)-methanol (0.256 g, 1.44 mmol) was dissolved in 5 mL anhydrous under N2. Anhydrous DMF (o. 111 mL, 1.44 mmol) was added followed by dropwise addition of POCl3 (0.134 mL, 1.44 mmol). The reaction was stirred at RT overnight. After 16 h the reaction was quenched by the addition of sat aq NaHCO3. The mixture was extracted 3× with DCM. The organic phases were dried over Na2SO4, filtered, and concentrated to provide the pure titled compound. 1H NMR (CDCl3) δ 8.33 (d, 1H, J=4.9 Hz), 7.44 (d, 1H, J=4.9 Hz), 4.68 (s, 2H).

Workup

  1. customAfter 16 h the reaction was quenched by the addition of sat aq NaHCO3
  2. extractionThe mixture was extracted 3× with DCM
  3. dry with materialThe organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-441d077c3e984b57b5d127b9e9c915a4
Source dataset
uspto-grants-2003_07
Patent number
US06586424B2

Reaction notes

Loading…