Thionyl Chloride → HCID 58248080, compound

HRID 2422180Notes

Reaction equation

HRID 2422180 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8](O)[CH3:9].S(Cl)([Cl:13])=O.C(=O)(O)[O-].[Na+]>O>[Cl:13][CH:8]([C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[F:1])[CH3:9]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 13129579HCID 13129579, compound

Product 1

HCID 58248080HCID 58248080, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

1-(3-fluoropyridin-4-yl)ethanol (0.8 g, 5.7 mmol) was treated with thionyl chloride (5 mL) and the resulting mixture was heated to 80° C. for 2 h. Water (10 mL) and sat. sodium bicarbonate (aq., 10 mL) was added. The product was extracted with DCM (three times). The combined organic extracts were washed with brine, dried over sodium sulphate and concentrated in vacuo. The crude product was purified by flash column chromatography (eluent heptane: ethyl acetate gradient) to yield 0.36 g (39% yield) of the title compound.

Workup

  1. extractionThe product was extracted with DCM (three times)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash column chromatography (eluent heptane: ethyl acetate gradient)

Sources & evidence

ORD record
ord-e1eca158726246368a3227984f013933
Source dataset
uspto-grants-2011_06
Patent number
US07960395B2

Reaction notes

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