Reaktion #316392

Reaktionsgleichung

(4-bromophenyl)(3-chloro-4-hydroxyphenyl)methanone

(4-Bromophenyl)(3-chloro-4-hydroxyphenyl)methanone

cycloheptanone

K2CO3

→

compound 124

Ausbeute 64.0%

4-[(4-Bromophenyl)(cycloheptylidene)methyl]-2-chlorophenol

Ausbeute 64.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat room temperature
2. 2
   TemperaturThe mixture was heated
3. 3
   Temperaturat reflux for 2 h
4. 4
   TemperaturThe reaction mixture was heated
5. 5
   Temperaturat reflux
6. 6
   FiltrationThe reaction mixture was filtered through a pad of Celite
7. 7
   Waschenthe pad was washed with EtOAc (100 mL)
8. 8
   SonstigeThe filtrate was transferred to a separatory funnel
9. 9
   Sonstigethe layers were separated
10. 10
    ExtraktionThe aqueous layer was further extracted with EtOAc (50 mL)
11. 11
    WaschenThe combined organic phase was washed with brine
12. 12
    Trocknendried over Na2SO4
13. 13
    Filtrationfiltered
14. 14
    Einengenthe filtrate was concentrated
15. 15
    Sonstigeto give the crude product as brown oil
16. 16
    SonstigeThe crude product was purified by flash chromatography on silica gel with hexanes:EtOAc (20:1)

Vorschrift

To a stirred suspension of zinc powder (1.35 g, 20.5 mmol) in THF (40 mL) was slowly added TiCl4 (1.13 mL, 10.3 mmol) via syringe at room temperature under a nitrogen atmosphere. The mixture was heated at reflux for 2 h. A solution of (4-bromophenyl)(3-chloro-4-hydroxyphenyl)methanone (105) (0.80 g, 2.57 mmol) and cycloheptanone (0.89 g, 7.70 mmol) in THF (15 mL) was added to the mixture. The reaction mixture was heated at reflux with stirring under a nitrogen atmosphere for 1.5 h. The reaction mixture was allowed to cool to room temperature. To the reaction mixture was slowly added 10% aqueous K2CO3 (40 mL). The reaction mixture was filtered through a pad of Celite and the pad was washed with EtOAc (100 mL). The filtrate was transferred to a separatory funnel and the layers were separated. The aqueous layer was further extracted with EtOAc (50 mL). The combined organic phase was washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as brown oil. The crude product was purified by flash chromatography on silica gel with hexanes:EtOAc (20:1) to give 0.64 g (64%) of compound 124 as a yellow viscous oil. 1H NMR (400 MHz, DMSO-d6): δ 1.50 (br s, 8H), 2.10-2.25 (m, 4H), 6.85-6.92 (m, 2H), 7.02 (br s, 1H), 7.07 (d, J=8.4 Hz, 2H), 7.47 (d, J=8.4 Hz, 2H), 10.1 (s, 1H). LCMS (APCI): m/z 413 (M+Na)+.

Quelle