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

HRID 1355465Notes

Reaction equation

HRID 1355465 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 (0.111 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) δ8.33 (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-5946d0b699154003ba775bf2422b99d3
Source dataset
uspto-grants-2003_07
Patent number
US06586423B2

Reaction notes

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