Dichloromethane → 5-(Chloromethyl)-2-methylpyridine

HRID 717747Notes

Reaction equation

HRID 717747 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][CH:3]=1.C(Cl)[Cl:11]>S(Cl)(Cl)=O>[Cl:11][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[N:7][CH:6]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 11228788(6-Methylpyridin-3-yl)methanol

Product 1

HCID 122143385-(Chloromethyl)-2-methylpyridine

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

To a stirred solution of (6-methylpyridin-3-yl)methanol (13 g) in DCM (260 mL), thionyl chloride (13 mL) was added slowly under nitrogen at RT. The mixture was stirred at RT for 1 h, the reaction was monitored by TLC and LCMS. After completion of reaction, the mixture was concentrated under reduced pressure, the residue was suspended in saturated aq. NaHCO3 (pH 8) and extracted with DCM (2×100 mL). The organic layer was separated, dried over sodium sulfate and concentrated under vacuum to obtain 12.5 g of product as a yellow oil.

Workup

  1. customAfter completion of reaction
  2. concentrationthe mixture was concentrated under reduced pressure
  3. extractionextracted with DCM (2×100 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-394dde992efd443181a11516359a9abe
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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