Sodium Bicarbonate → 5-Bromo-2-fluoro-1-benzofuran

HRID 383978

Reaktionsgleichung

Reaktionsgleichung von HRID 383978
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](C(O)=O)=[CH:7][C:6]=2[CH:13]=1.C(=O)(O)[O-].[Na+].[B-](F)(F)(F)[F:20].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(Cl)(Cl)(Cl)Cl.O.ClCCl.[OH-].[Na+]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([F:20])=[CH:7][C:6]=2[CH:13]=1

Komponenten

8

Edukt 3

HCID 516892Sodium BicarbonateHCID 7352475-Bromo-2-benzofurancarboxylic acidHCID 2724933Selectfluor

Produkt 1

HCID 574391135-Bromo-2-fluoro-1-benzofuran

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 5943Carbon TetrachlorideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

5-Bromobenzofuran-2-carboxylic acid (4.68 g) was suspended in carbon tetrachloride (150 ml) and water (50 ml). To this was added sodium bicarbonate (3.36 g), followed by Selectflor (7.1 g) and the reaction mixture was stirred rapidly for 20 hours. The reaction mixture was diluted with dichloromethane and 2N sodium hydroxide solution. The organic phase was separated, washed with brine and dried over anhydrous MgSO4. The solvent was evaporated under reduced pressure at room temperature. The residue was applied to a silica cartridge (20 g) and eluted with diethyl ether. This gave 5-bromo-2-fluoro-1-benzofuran (1.4 g).

Aufarbeitung

  1. customThe organic phase was separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. customThe solvent was evaporated under reduced pressure at room temperature
  5. washeluted with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-8f6c897831ea4099a94df7738e852e15
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367673B2

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