Thionyl Chloride → [(2-Chloroethyl)selanyl]benzene

HRID 977422Notes

Reaction equation

HRID 977422 reaction equation
[C:1]1([Se:7][CH2:8][CH2:9]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:13])=O>C(Cl)Cl>[Cl:13][CH2:9][CH2:8][Se:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Procedure

One gram of the resulting 2-hydroxyethyl phenyl selenide was dissolved in 15 ml of CH2Cl2. One ml of thionyl chloride was dissolved in 5 ml of CH2Cl2 and was added to the solution of the 2-hydroxyethyl phenyl selenide. The reaction mixture was refluxed for 1 h. The solvent was evaporated off and the remaining product transferred to a separatory funnel using CHCl3. Twenty ml of water was added to the separatory funnel and was made weakly basic with 5% aqueous NaHCO3. The CHCl3 layer was removed from the separatory funnel, dried with sodium sulfate and removed from the product by rotary evaporation and then in vacuo.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. customThe solvent was evaporated off
  3. customthe remaining product transferred to a separatory funnel
  4. additionTwenty ml of water was added to the separatory funnel
  5. customThe CHCl3 layer was removed from the separatory funnel
  6. dry with materialdried with sodium sulfate
  7. customremoved from the product by rotary evaporation

Sources & evidence

ORD record
ord-d7b4543fe6064b96a7353b5e431836e3
Source dataset
uspto-grants-1997_03
Patent number
US05614562

Reaction notes

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