Water → (5-Bromo-3-methylthiophen-2-yl)(4-propylphenyl)methanone

HRID 1469198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1469198
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=1)=[O:8].[Br-:18].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.O>C(O)(=O)C>[Br:18][C:5]1[S:4][C:3]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=2)=[O:8])=[C:2]([CH3:1])[CH:6]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 21124087PyridiniumtribromideHCID 43462760(3-Methylthiophen-2-yl)(4-propylphenyl)methanone

Produkt 1

HCID 66691033(5-Bromo-3-methylthiophen-2-yl)(4-propylphenyl)methanoneAusbeute 64,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of (3-methylthiophen-2-yl)(4-propylphenyl)methanone (44, 1.12 g, 4.58 mmol) in acetic acid (4.67 mL) was added pyridinium tribromide (3.67 g, 11.5 mmol). The reaction mixture was heated to 50° C. for 3 hours. After cooling to room temperature, the mixture was poured into water (50 mL) and extracted with EtOAc (100 mL). The organic phase was dried over MgSO4 and evaporated under vacuum. The residue was further purified by silica column chromatography (Biotage) to provide (5-bromo-3-methylthiophen-2-yl)(4-propylphenyl)methanone (45, 0.95 g, 2.95 mmol, 64%).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EtOAc (100 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. customevaporated under vacuum
  5. customThe residue was further purified by silica column chromatography (Biotage)

Quellen und Nachweise

ORD-Eintrag
ord-555aa7f58a6e4defb8dc4616d2e8bb12
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006187B2

Notizen zur Reaktion

Wird geladen…