Thionyl Chloride → 6-(Chloromethyl)-2,3-dihydrobenzofuran
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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).