Hydrochloric Acid → 2-Fluorobenzofuran-5-carbaldehyde

HRID 45627Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 45627
[Mg].II.Br[C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([F:13])=[CH:10][C:9]=2[CH:14]=1.Cl.[O:16]1CCC[CH2:17]1>[Cl-].[Na+].O.CN(C)C=O>[F:13][C:11]1[O:12][C:8]2[CH:7]=[CH:6][C:5]([CH:17]=[O:16])=[CH:14][C:9]=2[CH:10]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 8028Tetrahydrofuran2×HCID 5462224MagnesiumHCID 574391135-Bromo-2-fluoro-1-benzofuran

Produkt 1

HCID 450908312-Fluorobenzofuran-5-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A slurry of magnesium powder (219 mg) and iodine (cat) in dry tetrahydrofuran (3 ml) was heated at 50° C. under nitrogen for 20 minutes. 5-Bromo-2-fluoro-1-benzofuran (1.4 g) was dissolved in dry tetrahydrofuran (6 ml). A 1 ml portion of the solution was added to the slurry at 50° C. without stirring. After 30 minutes the rest of the solution was added slowly and the reaction was heated at reflux for 3 hours. The reaction was cooled in an ice/water bath and dimethylformamide (1 ml) was added dropwise maintaining the temperature below 10° C. After 1 hour a mixture of 2N hydrochloric acid (12.5 ml) and brine (12.5 ml) was added. The reaction mixture was extracted using ethyl acetate (3×25 ml). The combined organics were washed with brine and dried over anhydrous magnesium sulphate. The solvent was removed in vacuo and the residue applied to a silica cartridge (50 g). This was eluted with cyclohexane, cyclohexane/ethyl acetate (6:1, 5:1 v/v). This gave 2-fluoro-5-formyl-1-benzofuran (376 mg).

Aufarbeitung

  1. additionA 1 ml portion of the solution was added to the slurry at 50° C.
  2. additionAfter 30 minutes the rest of the solution was added slowly
  3. temperaturethe reaction was heated
  4. temperatureat reflux for 3 hours
  5. temperatureThe reaction was cooled in an ice/water bath
  6. temperaturemaintaining the temperature below 10° C
  7. additionwas added
  8. extractionThe reaction mixture was extracted
  9. washThe combined organics were washed with brine
  10. dry with materialdried over anhydrous magnesium sulphate
  11. customThe solvent was removed in vacuo
  12. washThis was eluted with cyclohexane, cyclohexane/ethyl acetate (6:1, 5:1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-f85faedff01e4a4cbbd3deb2185f6973
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541579B2

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