Thionyl Chloride → 2-(Chloromethyl)dibenzofuran

HRID 1620147Notes

Reaction equation

HRID 1620147 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:14]O.O=S(Cl)[Cl:18]>C(Cl)Cl>[Cl:18][CH2:14][C:2]1[CH:3]=[CH:4][C:5]2[O:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[C:9]=2[CH:1]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 2908462-Dibenzofuranmethanol2×

Product 1

HCID 2337372-(Chloromethyl)dibenzofuranYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Dibenzo[b,d]furan-2-ylmethanol CCH 34116 (174 mg, 878 μmol) was immediately dissolved in dry CH2Cl2 (10 mL) in a 20 mL microwave vial equipped with a magnetic stirrer before slow addition of SOCl2 (1.0 mL, 13.78 mmol) and the reaction mixture was stirred for 20 min at 80° C. under microwave irradiation. After cooling to RT, the volatiles were removed at 40° C. under vacuum. The residue was taken up in CH2Cl2 (20 mL) before concentration back to dryness at 40° C. under vacuum (done 3 times) to give 2-(chloromethyl)dibenzo[b,d]furan CCH 34116-2 as a grey solid (189 mg, 99% yield).

Workup

  1. temperatureAfter cooling to RT
  2. customthe volatiles were removed at 40° C. under vacuum
  3. concentrationThe residue was taken up in CH2Cl2 (20 mL) before concentration back to dryness at 40° C. under vacuum (done 3 times)

Sources & evidence

ORD record
ord-f2f0dfd07af549a0bcca5089d3fcbaeb
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

Loading…