Reaktion #162226

Reaktionsgleichung

bicyclo[2.2.1]hept-5-ene-3-carboxylic acid

NaHCO3

bromine

→

crude product

Ausbeute 67.7%

6-bromohexahydro-2H-3,5-methanocyclopenta[b]furan-2-one

Ausbeute 67.7%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ether
2. 2
   Waschenthe organic phase was washed successively with 1 N Na2S2SO3 solution and brine
3. 3
   Trocknenthe organic phase was then dried (Na2SO4)
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo

Vorschrift

To a solution of bicyclo[2.2.1]hept-5-ene-3-carboxylic acid (25.0 mL, 204.3 mmol) in NaHCO3 (51.5 g, 612.9 mmol) in water was added bromine (32.7 g, 204.3 mmol) dropwise at 0° C. The solution was stirred for 1 hour and extracted with ether, and the organic phase was washed successively with 1 N Na2S2SO3 solution and brine, and the organic phase was then dried (Na2SO4), filtered and concentrated in vacuo to afford 30 g of crude product that was used without further purification.

Quelle