Thionyl Chloride → HCID 117818697, compound

HRID 1753213Notes

Reaction equation

HRID 1753213 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:11]O)[C:5]([O:9][CH3:10])=[N:6][C:7]=1[CH3:8].S(Cl)([Cl:15])=O>C(Cl)Cl>[Cl:15][CH2:11][C:4]1[C:5]([O:9][CH3:10])=[N:6][C:7]([CH3:8])=[C:2]([F:1])[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 117818791HCID 117818791, compound

Product 1

HCID 117818697HCID 117818697, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-fluoro-2-methoxy-6-methylpyridin-3-yl)methanol (20) (0.2 g, 1.16 mmol) in DCM was added thionyl chloride (0.278 g, 2.33 mmol). The reaction mixture was stirred for 2 h at RT. The solvent was evaporated under the reduced pressure and the reaction mixture was poured in to water (50 mL) and extracted with DCM (2×50 mL). The combined organic layer was washed with water, brine, dried over sodium sulfate, and concentrated at reduced pressure to yield to afford 3-(chloromethyl)-5-fluoro-2-methoxy-6-methylpyridine (21) as a pale yellow liquid (0.2 g) 90%.

Workup

  1. customThe solvent was evaporated under the reduced pressure
  2. additionthe reaction mixture was poured in to water (50 mL)
  3. extractionextracted with DCM (2×50 mL)
  4. washThe combined organic layer was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated at reduced pressure
  7. customto yield

Sources & evidence

ORD record
ord-5a24156918ed4a7ab415bca373f88328
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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