Hydrochloric Acid → 6-Bromo-2-methyl-2-(trifluoromethyl)chroman-4-one

HRID 20054

Reaktionsgleichung

Reaktionsgleichung von HRID 20054
[C:1](O)(=O)CC(O)=O.[Br:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)O[C:14]([C:19]([F:22])([F:21])[F:20])=[CH:13]/[C:12]/2=N/CC1C=CC=CC=1.CCO.[OH2:34].Cl.[OH2:36]>O1CCOCC1>[Br:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:34][C:14]([CH3:1])([C:19]([F:20])([F:21])[F:22])[CH2:13][C:12]2=[O:36]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 962WaterHCID 19096565Water ethanolHCID 178506234HCID 178506234, Verbindung

Produkt 1

HCID 673056026-Bromo-2-methyl-2-(trifluoromethyl)chroman-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of malonic acid (1.2 ml, 19 mmol) and (Z)-N-(6-bromo-2-(trifluoromethyl)-4H-chromen-4-ylidene)(phenyl)methanamine (6.63 g, 17 mmol) in dioxane was heated to reflux for 18 h until the reaction was completed. The mixture was cooled to RT and treated with 50% EtOH/H2O (20 ml) followed by conc. HCl (5.0 ml). The resulted mixture was left to stand at RT for 40 min, and then diluted with water (500 ml). The product was extracted with hexane (3×300 ml). The organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel column (2-10% EtOAc/hexane) to afford the title compound as yellow oil. MS m/z: 310 (M+1).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 18 h until the reaction
  3. waitThe resulted mixture was left
  4. extractionThe product was extracted with hexane (3×300 ml)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel column (2-10% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c3a2be2fa62a4184bb7028072a2a91f8
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745484B2

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