Thionyl Chloride → HCID 58370159, compound

HRID 2062123Notes

Reaction equation

HRID 2062123 reaction equation
[F: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.O=S(Cl)[Cl:16]>ClCCl>[Cl:16][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:13])([F:12])[F:1])=[N:8][CH:7]=1)[CH3:10]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 497603801-(6-(Trifluoromethyl)pyridin-3-yl)ethanol

Product 1

HCID 58370159HCID 58370159, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.30 g of 1-(6-trifluoromethyl-pyridin-3-yl)-ethanol in 5 mL of dry dichloromethane was added 0.34 mL of SOCl2. The reaction mixture was refluxed for a half hour and then poured into ice-water, and extracted with dichloromethane. The organic phase was washed with 10% aqueous sodium hydrogen carbonate solution, dried over sodium sulphate and concentrated in vacuo. The resulting residue was purified by flash chromatography (silica, heptanes/ethyl acetate) to give 0.10 g of 5-(1-chloroethyl)-2-trifluoromethyl-pyridine.

Workup

  1. temperatureThe reaction mixture was refluxed for a half hour
  2. extractionextracted with dichloromethane
  3. washThe organic phase was washed with 10% aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by flash chromatography (silica, heptanes/ethyl acetate)

Sources & evidence

ORD record
ord-6f9a2b0b6e474694b39bb246f627b4ae
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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