Water → 2-Chloromethylbenzofuran

HRID 2372751Notes

Reaction equation

HRID 2372751 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10]O.S(Cl)([Cl:14])=O.O>C(Cl)(Cl)Cl.ClCCl>[Cl:14][CH2:10][C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 27762631-Benzofuran-2-Ylmethanol

Product 1

HCID 1843482-ChloromethylbenzofuranYield 80%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A three-necked flask is charged with 33.2 g of 2-benzofuranylmethanol dissolved in 450 ml of anhydrous chloroform, 48.8 ml of thionyl chloride are then introduced dropwise and the temperature is raised gently to reflux and maintained for 3 hours 30 minutes. The reaction medium is then cooled and poured into 1 l of water, and is thereafter diluted with 500 ml of dichloromethane. After settling has taken place, the organic phase is washed to neutrality and dried over anhydrous magnesium sulfate, the solvent is evaporated off and the residue is distilled under vacuum to obtain the expected compound.

Workup

  1. temperaturethe temperature is raised gently
  2. temperatureto reflux
  3. temperaturemaintained for 3 hours 30 minutes
  4. temperatureThe reaction medium is then cooled
  5. washthe organic phase is washed to neutrality
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent is evaporated off
  8. distillationthe residue is distilled under vacuum

Sources & evidence

ORD record
ord-60a1b76788794be7aed25d94e96b5c88
Source dataset
uspto-grants-1992_03
Patent number
US05100902

Reaction notes

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