Thionyl Chloride → HCID 72210972, compound

HRID 1753208Notes

Reaction equation

HRID 1753208 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9]O)=[CH:7][C:6]([C:11]([F:14])([F:13])[F:12])=[CH:5][N:4]=1.S(Cl)([Cl:17])=O>C(Cl)Cl>[Cl:17][CH2:9][C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 71650743[2-Methoxy-5-(trifluoromethyl)pyridin-3-yl]methanol

Product 1

HCID 72210972HCID 72210972, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methoxy-5-(trifluoromethyl)pyridin-3-yl)methanol (14) (0.4 g, 1.93 mmol) dissolved in DCM was added thionyl chloride (0.38 ml, 3.86 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 3-(chloromethyl)-2-methoxy-5-(trifluoromethyl)pyridine (15) as a liquid. (Yield 0.3 g, 69.76%)

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

Sources & evidence

ORD record
ord-7283ac78413746a4a5751cea2b105110
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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