Thionyl Chloride → 5-Chloromethyl-6-fluoro-benzo[1,3]dioxole

HRID 1991611Notes

Reaction equation

HRID 1991611 reaction equation
[F:1][C:2]1[C:3]([CH2:11]O)=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.C([O-])(O)=O.[Na+].O=S(Cl)[Cl:20]>>[Cl:20][CH2:11][C:3]1[C:2]([F:1])=[CH:10][C:6]2[O:7][CH2:8][O:9][C:5]=2[CH:4]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 591291851,3-Benzodioxole-5-methanol, 6-fluoro-

Product 1

HCID 591292085-Chloromethyl-6-fluoro-benzo[1,3]dioxoleYield 90%

Procedure

(6-Fluoro-benzo[1,3]dioxol-5-yl)-methanol (650 mg, 3.8 mmol) was added to SOCl2 (20 mL) in portions at 0° C. The mixture was warmed to room temperature for 1 h and then heated at reflux for 1 h. The excess SOCl2 was evaporated under reduced pressure to give the crude product, which was basified with sat. NaHCO3 solution to pH ˜7. The aqueous phase was extracted with EtOAc (50 mL×3). The combined organic layers were dried over Na2SO4 and evaporated under reduced pressure to give 5-chloromethyl-6-fluoro-benzo[1,3]dioxole (640 mg, 90%), which was directly used in the next step.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 h
  3. customThe excess SOCl2 was evaporated under reduced pressure
  4. customto give the crude product, which
  5. extractionThe aqueous phase was extracted with EtOAc (50 mL×3)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5d2ad0db0c074df29cb0482fe4dd5c22
Source dataset
uspto-grants-2010_01
Patent number
US07645789B2

Reaction notes

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