3-(4-Bromothiophenoxy)propionic acid → 6-Bromo-2,3-dihydro-4H-1-benzothiopyran-4-one

HRID 619591Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 619591
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([S:6][CH2:7][CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1>CS(O)(=O)=O.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:6][CH2:7][CH2:8][C:9](=[O:11])[C:12]=2[CH:13]=1

Komponenten

4

Edukt 1

HCID 167762423-(4-Bromothiophenoxy)propionic acid

Produkt 1

HCID 139537366-Bromo-2,3-dihydro-4H-1-benzothiopyran-4-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6395Methanesulfonic AcidLösungsmittel

Versuchsvorschrift

A solution of 3.63 g (13.9 mmol) of 3-(4-bromothiophenoxy)propionic acid in 60 ml methanesulfonic acid was heated to 75° C. for 1.5 hours. After cooling to room temperature the solution was diluted with H2O and extracted with EtOAc. The combined organic layers were washed with 2N aqueous NaOH, H2O, and saturated aqueous NaCl and then dried over MgSO4. Removal of the solvent under reduced pressure afforded a yellow solid from which the product was isolated by column chromatography (3% hexanes) as a pale-yellow solid. 1H NMR (CDCl3): δ 8.22 (1H, d, J=2.1 Hz), 7.48 1H, dd, J=2.1, 8.3 Hz), 7.17 (1H, d, J=8.5 Hz), 3.24 (2H, t, J=6.4 Hz), 2.98 (2H, t, J=6.7 Hz).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with 2N aqueous NaOH, H2O, and saturated aqueous NaCl
  3. dry with materialdried over MgSO4
  4. customRemoval of the solvent under reduced pressure
  5. customafforded a yellow solid from which the product

Quellen und Nachweise

ORD-Eintrag
ord-dcc9bae2a92c4dd3b5257facd60ebd1f
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05958954

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