Hydrochloric Acid → HCID 66777791, compound

HRID 2091042Notes

Reaction equation

HRID 2091042 reaction equation
Br[CH2:2][C:3]1[C:7]2[CH:8]=[C:9]([F:12])[CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[C:13]([O:15][CH3:16])=[O:14].[CH3:17][O-:18].[Na+].Cl>CO>[F:12][C:9]1[CH:10]=[CH:11][C:6]2[O:5][C:4]([C:13]([O:15][CH3:16])=[O:14])=[C:3]([CH2:2][O:18][CH3:17])[C:7]=2[CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 66778012HCID 66778012, compound

Product 1

HCID 66777791HCID 66777791, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution (50 mL) of methyl 3-(bromomethyl)-5-fluoro-1-benzofuran-2-carboxylate (5.87 g) synthesized above in methanol was added 28% solution (8.33 mL) of sodium methoxide in methanol, and the mixture was stirred with heating under reflux for 3 hr. 1N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (50% ethyl acetate/hexane) to give the title object compound (3.04 g, 63%) as a white solid.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 3 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-92ba5144fe3e480cbdf5dafd1b9af565
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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