Thionyl Chloride → Pyridine, 2-(chlorodifluoromethyl)-5-(1-chloroethyl)-

HRID 1931367Notes

Reaction equation

HRID 1931367 reaction equation
[Cl:1][C:2]([F:13])([F:12])[C:3]1[N:8]=[CH:7][C:6]([CH:9](O)[CH3:10])=[CH:5][CH:4]=1.S(Cl)([Cl:16])=O>C(Cl)Cl>[Cl:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]([Cl:16])[CH3:10])=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 592186063-Pyridinemethanol, 6-(chlorodifluoromethyl)-alpha-methyl-

Product 1

HCID 59218619Pyridine, 2-(chlorodifluoromethyl)-5-(1-chloroethyl)-Yield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{6-[chloro(difluoro)methyl]pyridin-3-yl}ethanol (0.78 g, 3.77 mmol) in CH2Cl2 (40 mL) was added thionyl chloride (0.54 mL, 7.54 mmol) dropwise at room temperature. After 1 hr, the reaction was quenched slowly with saturated NaHCO3 aqueous solution and the two phases were separated. The organic layer was dried over Na2SO4, filtered, concentrated, and dried in vacuum to give 0.83 g of the crude 2-[chloro(difluoro)methyl]-5-(1-chloroethyl)pyridine (D) as brown oil in 98% yield, which was directly used for the next step reaction. GC-MS: mass calcd for C8H7Cl2F2N [M]+ 225. Found 225.

Workup

  1. customthe reaction was quenched slowly with saturated NaHCO3 aqueous solution
  2. customthe two phases were separated
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customdried in vacuum

Sources & evidence

ORD record
ord-680a4e4f66fb4f2d9562e45b80e8c29b
Source dataset
uspto-grants-2012_05
Patent number
US08188292B2

Reaction notes

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