Thionyl Chloride → 4-(tert-Butyl)-2-(chloromethyl)pyridine

HRID 963491Notes

Reaction equation

HRID 963491 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11]O)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:15])=O>C(Cl)(Cl)Cl>[C:1]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][Cl:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 18799645(4-(tert-Butyl)pyridin-2-yl)methanol

Product 1

HCID 190813024-(tert-Butyl)-2-(chloromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of 4-tert-butyl-2-hydroxymethylpyridine (0.36 g) in chloroform (10 ml) was added dropwise a solution of thionyl chloride (1 ml) in chloroform (5 ml) at room temperature and the mixture was stirred for 3 hours at ca. 50° C., After cooling to room temperature, the resultant mixture was concentrated in vacuo. The residue was taken up with chloroform and washed with saturated sodium carbonate aqueous solution, dried over magnesium sulfate, filtered and concentrated in vacuo to give 4-tert-butyl-2-chloromethylpyridine (0.37 g) as a brown oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe resultant mixture was concentrated in vacuo
  3. washwashed with saturated sodium carbonate aqueous solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a8966bd26994a7598edcf4c7e6a2a0c
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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