Phosphorus oxybromide → 1-Bromo-6-(2-ethyl-6-methyl-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester

HRID 409255Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 409255
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10](O)[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:27][CH3:28])=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].P(Br)(Br)([Br:32])=O>CC#N>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([Br:32])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:27][CH3:28])=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Komponenten

4

Edukt 2

HCID 24613Phosphorus oxybromideHCID 178450851HCID 178450851, Verbindung

Produkt 1

HCID 866170731-Bromo-6-(2-ethyl-6-methyl-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid butyl esterAusbeute 34,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 6-(2-Ethyl-6-methyl-phenoxy)-1,4-dihydroxy-isoquinoline-3-carboxylic acid butyl ester (2.83 mmol, 1.12 g), POBr3 (11 mmol, 3.19 g), MeCN (20 mL) was refluxed gently with stirring for 1 h before it was concentrated in vacuo. The residue was dissolved in CHCl3 (50 mL). Water (10 mL) and subsequently small portions of NaHCO3 (6 g) were added with stirring. The mixture was stirred for 30 min at ambient temperature before it was filtered through a pad of celite. The filtrate was dried over MgSO4. Concentration and purification of the residue by flash column chromatography on silica gel using CH2Cl2 as the eluent gave the title compound as a tan oil (450 mg); MS-(+)-ion: M+1, 79Br/81Br=458.4 and 460.6.

Aufarbeitung

  1. temperaturewas refluxed gently
  2. concentrationwas concentrated in vacuo
  3. dissolutionThe residue was dissolved in CHCl3 (50 mL)
  4. additionWater (10 mL) and subsequently small portions of NaHCO3 (6 g) were added
  5. stirringwith stirring
  6. stirringThe mixture was stirred for 30 min at ambient temperature before it
  7. filtrationwas filtered through a pad of celite
  8. dry with materialThe filtrate was dried over MgSO4
  9. concentrationConcentration and purification of the residue by flash column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f3d9751e92d24d9faea014ba5259e3c9
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759373B2

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