Dichloromethane → Pyridine, 4,5-bis(chloromethyl)-2-(trifluoromethyl)-

HRID 1930818Notes

Reaction equation

HRID 1930818 reaction equation
OC[C:3]1[C:4]([CH2:13]O)=[CH:5][C:6]([C:9]([F:12])([F:11])[F:10])=[N:7][CH:8]=1.S(Cl)([Cl:17])=O.Cl[CH2:20][Cl:21]>>[Cl:17][CH2:13][C:4]1[C:3]([CH2:20][Cl:21])=[CH:8][N:7]=[C:6]([C:9]([F:12])([F:11])[F:10])[CH:5]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 586879226-(Trifluoromethyl)-3,4-pyridinedimethanol

Product 1

HCID 57753353Pyridine, 4,5-bis(chloromethyl)-2-(trifluoromethyl)-Yield 66%

Procedure

To a room temperature suspension of 2.5 mmol (5-Hydroxymethyl-2-trifluoromethyl-pyridin-4-yl)-methanol (CAS: 765298-25-7) in 3 ml dichloromethane was added dropwise 12.5 mmol thionylchloride. After 1 hour, the reaction mixture was evaporated in vacuo. The residue was dissolved in dichloromethane and washed with saturated sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a light yellow oil (66% yield). MS (m/e): 243.0 (M−H, 100%)

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with saturated sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography (SiO2, heptane/ethyl acetate)

Sources & evidence

ORD record
ord-27d43fdd2c214859a81ac22d9f395054
Source dataset
uspto-grants-2012_05
Patent number
US08188139B2

Reaction notes

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