Thionyl Chloride → 6-(Chloromethyl)-2,3-dihydrobenzofuran

HRID 869868Notes

Reaction equation

HRID 869868 reaction equation
[O:1]1[C:5]2[CH:6]=[C:7]([CH2:10]O)[CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.O=S(Cl)[Cl:14]>C(Cl)(Cl)Cl>[Cl:14][CH2:10][C:7]1[CH:8]=[CH:9][C:4]2[CH2:3][CH2:2][O:1][C:5]=2[CH:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 18356898(2,3-Dihydrobenzofuran-6-yl)methanol

Product 1

HCID 215538426-(Chloromethyl)-2,3-dihydrobenzofuranYield 80%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of (2,3-dihydrobenzofuran-6-yl)methanol (13.8 g, 92 mmol) in CHCl3 (200 mL) was slowly added SOCl2 at 0□. The reaction mixture was stirred at reflux for 4 h. After the solvent was removed, saturated NaHCO3 and ethyl acetate were added to the mixture. The organic layer was extracted with ethyl acetate. The combined organic layer was then washed with brine and dried over Na2SO4, filtered and concentrated to afford 6-(chloromethyl)-2,3-dihydrobenzofuran (12.3 g, 80.0% yield). 1H NMR (400 MHz, CDCl3) δ: 7.16 (d, J=7.5, 1H), 6.87 (d, J=7.5, 1H), 6.83 (s, 1H), 4.58 (t, J=8.7, 2H), 4.49 (s, 2H), 3.20 (t, J=8.7, 2H).

Workup

  1. temperatureat reflux for 4 h
  2. customAfter the solvent was removed
  3. additionsaturated NaHCO3 and ethyl acetate were added to the mixture
  4. extractionThe organic layer was extracted with ethyl acetate
  5. washThe combined organic layer was then washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6871aa3dce0d4047ace83bf9b4ca038f
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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