Ethyl 4-(4-bromobenzoyl)benzoate → HCID 67341340, Verbindung

HRID 1669281Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1669281
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)[CH3:2].[CH2:21]([Mg]Br)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>C1COCC1>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:6]=[CH:7][C:8]([C:11]([C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)([OH:19])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:9][CH:10]=1)[CH3:2]

Komponenten

4

Edukt 2

HCID 24722740Ethyl 4-(4-bromobenzoyl)benzoateHCID 178444609HCID 178444609, Verbindung

Produkt 1

HCID 67341340HCID 67341340, VerbindungAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-(4-Bromo-benzoyl)-benzoic acid ethyl ester (2.0 g, 6 mmol) in THF (20 mL) at 0° C. is added hexylmagnesium bromide (2M, 3.3 mL). After stirring at room temperature for 2 hours, it is quenched with saturated ammonium chloride, extracted with EtOAc. The organic is concentrated and purified by column chromatography to give 4-[1-(4-Bromo-phenyl)-1-hydroxy-heptyl]-benzoic acid ethyl ester (0.48 g, 19%), which is taken into methanol (2 mL), treated with sodium hydroxide (5N aqueous, 1 mL) for 3 h at room temperature. The mixture is concentrated, diluted with ethyl acetate, acidified with 5 N HCl (1.1 mL), extracted with ethyl acetate. The organic layers are dried and concentrated giving to afford the titled compound (0.47 g).

Aufarbeitung

  1. customit is quenched with saturated ammonium chloride
  2. extractionextracted with EtOAc
  3. concentrationThe organic is concentrated
  4. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-602d730a90ea482995583c873a041139
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989457B2

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