Acetyl chloride → 7-bromo-3,4-dihydro-1H-2-benzopyran-1,3-dione

HRID 506967Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 506967
[C:1]([CH2:4][C:5]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(O)=[O:2].C(Cl)(=O)C>CC(C)=O>[Br:14][C:11]1[CH:10]=[C:6]2[C:5]([CH2:4][C:1](=[O:2])[O:8][C:7]2=[O:9])=[CH:13][CH:12]=1

Komponenten

4

Edukt 2

HCID 6367Acetyl chlorideHCID 106349875-Bromo-2-(carboxymethyl)benzoic acid

Produkt 1

HCID 185077967-bromo-3,4-dihydro-1H-2-benzopyran-1,3-dioneAusbeute 99,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a suspension of 2-(carboxymethyl)-5-bromobenzoic acid (2.37 g) in acetone (20 ml) was added acetyl chloride (2.60 ml) and the reaction mixture was stirred at room temperature for 18 hours. The solvent was evaporated and azeotroped with toluene (×3). The resultant solid was triturated with diethyl ether to yield 7-bromo-1H-isochromene-1,3(4H)-dione as a brown solid (2.20 g); NMR Spectrum: (DMSOd6) 4.24 (s, 2H), 7.42 (d, 1H), 7.94 (d, 1H), 8.13 (s, 1H).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customazeotroped with toluene (×3)
  3. customThe resultant solid was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-b61d3480532f4df98c930fc08176f129
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786115B2

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