Thionyl Chloride → 2-Chloromethylbenzofuran

HRID 1091079Notes

Reaction equation

HRID 1091079 reaction equation
S(Cl)([Cl:3])=O.[O:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH:7]=[C:6]1[CH2:14]O>N1C=CC=CC=1.ClCCl.O>[Cl:3][CH2:14][C:6]1[O:5][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH:7]=1

Participants

6

Reactant 2

HCID 24386Thionyl ChlorideHCID 27762631-Benzofuran-2-Ylmethanol

Product 1

HCID 1843482-ChloromethylbenzofuranYield 70.8%

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (5.14 mL, 70.46 mmol) was added dropwise to a solution of benzofuran-2-methanol (3.58 g, 23.48 mmol) and pyridine (10 drops) in dichloromethane (60 mL). Stirring was continued at room temperature for 18 hours. The mixture was carefully diluted with water and extracted with methylene chloride. The organic extracts were washed with aqueous sodium bicarbonate, dried (MgSO4) and concentrated to afford crude product which was purified by flash column chromatography (10% ethyl acetate/hexanes) to afford 2.77 g (69%) of pure product as a yellow oil.

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic extracts were washed with aqueous sodium bicarbonate
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto afford crude product which
  6. customwas purified by flash column chromatography (10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2611c20359a248e0bb5cf59284a8dcb3
Source dataset
uspto-grants-1992_01
Patent number
US05084463

Reaction notes

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