Reaktion #81714

Reaktionsgleichung

methyl 2-(4'-hydroxymethylphenyl)benzoate

phosphorus tribromide

sodium hydrogencarbonate

→

title compound

Ausbeute 100.4%

methyl 2-(4'-bromomethylphenyl)benzoate

Ausbeute 100.4%

Lösungsmittel

pyridine

n-hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder cooling with ice
2. 2
   SonstigeThe reaction liquid
3. 3
   Extraktionfollowed by the extraction with n-hexane
4. 4
   WaschenThe organic phase was washed with water
5. 5
   Sonstigedried
6. 6
   Einengensubjected to vacuum concentration
7. 7
   SonstigeThe residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system)

Vorschrift

10.0 g (41 mmol) of methyl 2-(4'-hydroxymethylphenyl)benzoate was dissolved in 7.9 g of pyridine and n-hexane (100 ml). 8.3 g (31 mmol) of phosphorus tribromide was dropwise added thereto under cooling with ice, followed by stirring for 2 hours as such. The reaction liquid was added to an aqueous solution of sodium hydrogencarbonate, followed by the extraction with n-hexane. The organic phase was washed with water, dried and subjected to vacuum concentration. The residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system) to give 9.5 g of the title compound (yield 75%).

Quelle