Sodium Bicarbonate → 5-Bromo-2-fluoro-6-methyl-benzofuran

HRID 874671Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 874671
[Br:1][C:2]1[C:3]([CH3:14])=[CH:4][C:5]2[O:9][C:8](C(O)=O)=[CH:7][C:6]=2[CH:13]=1.[B-](F)(F)(F)[F:16].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.C(=O)(O)[O-].[Na+]>O.CC(=O)OCC>[Br:1][C:2]1[C:3]([CH3:14])=[CH:4][C:5]2[O:9][C:8]([F:16])=[CH:7][C:6]=2[CH:13]=1

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 2724933Selectfluor2×HCID 671269275-Bromo-6-methylbenzofuran-2-carboxylic acid

Produkt 1

HCID 584873945-Bromo-2-fluoro-6-methyl-benzofuranAusbeute 36,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

A mixture of 5-bromo-6-methyl-benzofuran-2-carboxylic acid (229, 243 mg, 0.95 mmol), Selectfluor (481 mg, 1.36 mmol) and sodium bicarbonate (228 mg, 2.72 mmol) in 3 ml water and 3 ml EA was stirred vigorously at r.t. for 60 h before addition of another 240 mg of Selectfluor. After further 20 h the reaction mixture was diluted with EA, washed twice with 1N NaOH. Org phase was washed with brine, dried over sodium sulfate, concentrated to dryness to give 78.5 mg of title compound as light brown wax (yield: 36.1%, purity>95%).

Aufarbeitung

  1. washwashed twice with 1N NaOH
  2. washOrg phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-80082744764f4dd183d3ef152e95bdb5
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980629B2

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