Thionyl Chloride → 5-(Chloromethyl)-2-methoxypyridine

HRID 1896244Notes

Reaction equation

HRID 1896244 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[N:12]=[CH:11][C:10]([CH2:13]O)=[CH:9][CH:8]=1>C(Cl)Cl>[Cl:3][CH2:13][C:10]1[CH:9]=[CH:8][C:7]([O:6][CH3:5])=[N:12][CH:11]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12259941(6-Methoxypyridin-3-yl)methanol

Product 1

HCID 137528915-(Chloromethyl)-2-methoxypyridineYield 216.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.23 ml, 3.23 mmol) was added to a solution of (6-methoxypyridin-3-yl)methanol (1.10 g, 8.41 mmol) in DCM at 0° C. and the reaction mixture was stirred for 2 h at room temperature. After completion of reaction, the volatiles were evaporated and the reaction mixture was basified with saturated sodium bicarbonate solution. The compound was extracted with DCM (2×30 ml) and washed with brine (15 ml). The organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and dried to afford 1.1 g (88%) of 5-(chloromethyl)-2-methoxypyridine as a colorless liquid. This compound was directly taken to the next step.

Workup

  1. customAfter completion of reaction
  2. customthe volatiles were evaporated
  3. extractionThe compound was extracted with DCM (2×30 ml)
  4. washwashed with brine (15 ml)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried

Sources & evidence

ORD record
ord-58a2677de3c94effa800d4ef161ad027
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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