Dichloromethane → 4-(Chloromethyl)-2-methylpyridine

HRID 77913Notes

Reaction equation

HRID 77913 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8]O)[CH:5]=[CH:4][N:3]=1.S(Cl)([Cl:12])=O.C(Cl)Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[Cl:12][CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 9942144(2-Methylpyridin-4-yl)methanol

Product 1

HCID 126752624-(Chloromethyl)-2-methylpyridine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

(2-Methyl-pyridin-4-yl)-methanol (40 mg, 0.33 mmol) described in Manufacturing Example 47-1-1, thionyl chloride (0.047 ml, 0.65 mmol) and methylene chloride (4.0 ml) were stirred for 5 minutes at 60° C. Sodium bicarbonate solution and ethyl acetate were added to separate the reaction solution, and the ethyl acetate layer was dried over sodium sulfate. The solvent was evaporated under a reduced pressure to obtain 4-chloromethyl-2-methyl-pyridine as a crude product.

Workup

  1. customto separate the reaction solution
  2. dry with materialthe ethyl acetate layer was dried over sodium sulfate
  3. customThe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-b03c9a7a8fb94143b82443660a012130
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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