Calcium Carbonate → 6-fluoro-3H-isobenzofuran-1-one

HRID 2361285Notes

Reaction equation

HRID 2361285 reaction equation
BrC[C:3]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[Ca+2]>O1CCOCC1.O>[F:13][C:10]1[CH:9]=[C:4]2[C:3]([CH2:8][O:7][C:5]2=[O:6])=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 10112Calcium CarbonateHCID 15155455Methyl 2-(bromomethyl)-5-fluorobenzoate

Product 1

HCID 111710826-fluoro-3H-isobenzofuran-1-oneYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 2-(bromomethyl)-5-fluorobenzoate (0.750 g, 3.04 mmol) and calcium carbonate (1.823 g, 18.21 mmol) in 1,4-dioxane (30 mL) and water (30.0 mL) was heated at reflux for 2.5 hr. The insoluble material was removed by filtration. The filtrate was concentrated under vacuum and then extracted with CH2Cl2 (4×30 mL). The combined extract was dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product (0.423 g, 2.78 mmol, 92% yield) as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hr
  3. customThe insoluble material was removed by filtration
  4. concentrationThe filtrate was concentrated under vacuum
  5. extractionextracted with CH2Cl2 (4×30 mL)
  6. extractionThe combined extract
  7. dry with materialwas dried over anhydrous MgSO4
  8. customRemoval of solvent under vacuum

Sources & evidence

ORD record
ord-1d39b7fe63c14925a9f9c1401874f7d7
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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