Reaktion #536308

Reaktionsgleichung

HCl

aluminum trichloride

4-bromo-naphthalene-1-carboxylic acid

thionyl chloride

→

(4-Bromo-naphthalen-1-yl)-phenyl-methanone

Lösungsmittel

DMF

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigean oven dried flask
2. 2
   workup.DISTILLATIONThe thionyl chloride was then distilled off
3. 3
   SonstigeThe crude reaction mixture
4. 4
   SonstigeThe organic layer was separated
5. 5
   Extraktionthe aqueous layer extracted with EtOAc
6. 6
   WaschenThe combined organic phases were washed with 5% aq NaOH solution, water
7. 7
   Trocknendried (Na2SO4)
8. 8
   EinengenThe organic phase was concentrated in vacuo
9. 9
   Sonstigeto give a residue which
10. 10
    Sonstigewas purified by silica gel chromatography
11. 11
    Wascheneluting with 2% EtOAc in hexane

Vorschrift

an oven dried flask was added 4-bromo-naphthalene-1-carboxylic acid In (1.36 g, 0.0054 mol), thionyl chloride (0.77 mL, 0.010 mol) and a drop of DMF and the reaction was refluxed for 2 h. The thionyl chloride was then distilled off and benzene (20 mL) and aluminum trichloride (0.676 g, 0.0051 mol) was added to the reaction mixture and the reaction was stirred at room temp for 1 h. The crude reaction mixture was poured onto ice and conc HCl (15 mL). The organic layer was separated and the aqueous layer extracted with EtOAc. The combined organic phases were washed with 5% aq NaOH solution, water and dried (Na2SO4). The organic phase was concentrated in vacuo to give a residue which was purified by silica gel chromatography, eluting with 2% EtOAc in hexane.

Quelle