Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → 7-Bromo-4-(4-fluorophenyl)-6-methyl-2H-chromen-2-one

HRID 1988193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1988193
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=O)=[C:4]([OH:18])[CH:3]=1.C[O:20][C:21](=O)[CH:22]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)=[CH:22][C:21](=[O:20])[O:18]2)=[CH:6][C:7]=1[CH3:8]

Komponenten

4

Edukt 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 57729256(4-Bromo-2-hydroxy-5-methylphenyl)(4-fluorophenyl)methanone

Produkt 1

HCID 577292547-Bromo-4-(4-fluorophenyl)-6-methyl-2H-chromen-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

(4-Bromo-2-hydroxy-5-methylphenyl)(4-fluorophenyl)methanone (1.61 g, 5.21 mmol) and methyl(triphenylphosphoranylidene)acetate (2.26 g, 6.77 mmol) were heated in refluxing toluene (15 mL) for 24 h. The reaction mixture was allowed to cool to rt and concentrated. The yellow solid obtained was subjected to column chromatography on silica gel (EtOAc-toluene, 0% to 2%) to afford the title compound. 1H NMR (500 MHz, acetone-d6): δ 7.70 (s, 1H), 7.66 (m, 2H), 7.46 (s, 1H), 7.39 (m, 2H), 6.39 (s, 1H), 2.40 (s, 3H).

Aufarbeitung

  1. concentrationconcentrated
  2. customThe yellow solid obtained

Quellen und Nachweise

ORD-Eintrag
ord-15d9ca8a00c04564ae20d9603e71dd62
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07553973B2

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