Pyridine → 2-(4-Iodophenyl)ethylchloride

HRID 1978038Notes

Reaction equation

HRID 1978038 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]O)=[CH:4][CH:3]=1.N1C=CC=CC=1.S(Cl)([Cl:19])=O>C(Cl)(Cl)Cl>[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][Cl:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 30407702-(4-Iodophenyl)ethan-1-ol

Product 1

HCID 158961892-(4-Iodophenyl)ethylchlorideYield 99%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a 500 mL round-bottomed flask equipped with dropping funnel, condenser and N2 inlet were added 307 g (124 mmol) 2-(4-iodophenyl)ethanol, 200 mL chloroform, and 10.0 mL (124 mmol) pyridine. A solution of 13.5 mL (186 mmol) thionyl chloride in 50 mL chloroform was added dropwise over 15 min, and the reaction then heated at reflux for 2 hr. The reaction was cooled, the solvent evaporated, and the residue taken up in ethyl acetate, washed with 1 N hydrochloric acid, water, saturated aqueous sodium bicarbonate solution and brine, dried, and evaporated. The resulting oil was chromatographed on silica gel using 20% ethyl acetate in hexane as eluant to afford 32.6 g (99%) of the product as an oil.

Workup

  1. customTo a 500 mL round-bottomed flask equipped
  2. customthe reaction
  3. temperaturethen heated
  4. temperatureat reflux for 2 hr
  5. temperatureThe reaction was cooled
  6. customthe solvent evaporated
  7. washwashed with 1 N hydrochloric acid, water, saturated aqueous sodium bicarbonate solution and brine
  8. customdried
  9. customevaporated
  10. customThe resulting oil was chromatographed on silica gel using 20% ethyl acetate in hexane as eluant

Sources & evidence

ORD record
ord-a5acaaa9ec28433c92cf48ebfd3b5ade
Source dataset
uspto-grants-2001_05
Patent number
US06235747B1

Reaction notes

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