Thionyl Chloride → 6-(Chloromethyl)-4-fluorobenzo[d][1,3]dioxole

HRID 468283Notes

Reaction equation

HRID 468283 reaction equation
[F:1][C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=[C:4]([CH2:11]O)[CH:3]=1.C([O-])(O)=O.[Na+].O=S(Cl)[Cl:20]>>[Cl:20][CH2:11][C:4]1[CH:3]=[C:2]([F:1])[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 59129331(7-Fluoro-benzo[1,3]dioxol-5-yl)-methanol

Product 1

HCID 591293256-(Chloromethyl)-4-fluorobenzo[d][1,3]dioxoleYield 92%

Procedure

To SOCl2 (20 mL) was added (7-fluoro-benzo[1,3]dioxol-5-yl)-methanol (0.80 g, 4.7 mmol) in portions at 0° C. The mixture was warmed to room temperature over 1 h and then was heated at reflux for 1 h. The excess SOCl2 was evaporated under reduced pressure to give the crude product, which was basified with saturated aqueous NaHCO3 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 6-chloromethyl-4-fluoro-benzo[1,3]dioxole (0.80 g, 92%), which was directly used in the next step.

Workup

  1. temperaturewas heated
  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-204ea736085b4d44937ed412e0666711
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

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