Dichloromethane → 3-(Chloromethyl)-2-methylpyridine

HRID 2070949Notes

Reaction equation

HRID 2070949 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8]O)=[CH:6][CH:5]=[CH:4][N:3]=1.C(Cl)[Cl:11]>>[Cl:11][CH2:8][C:7]1[C:2]([CH3:1])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 302564(2-Methylpyridin-3-yl)methanol

Product 1

HCID 122437113-(Chloromethyl)-2-methylpyridine

Procedure

To a stirring solution of crude (2-methylpyridin-3-yl)methanol in 20 mL of CH2Cl2 was added 2.2 mL of SO2Cl2. After 17 h the solution was concentrated and CH2Cl2 and saturated NaHCO3 were added. The layers were separated, and the organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (1% MeOH/CHCl3) provided 1.18 g of 3-(chloromethyl)-2-methylpyridine as yellow-orange oil.

Workup

  1. concentrationAfter 17 h the solution was concentrated
  2. additionCH2Cl2 and saturated NaHCO3 were added
  3. customThe layers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash silica gel chromatography (1% MeOH/CHCl3)

Sources & evidence

ORD record
ord-6f5f0122ebca4aff8852d13af316a7c8
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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