Bromine → 6-Bromohexahydro-2h-3,5-methanocyclopenta[b]furan-2-one
Reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH:3]([C:8]([OH:10])=[O:9])[CH2:2]2.C([O-])(O)=O.[Na+].[Br:16]Br>O>[Br:16][CH:6]1[CH:5]2[O:9][C:8](=[O:10])[CH:3]3[CH2:2][CH:1]1[CH2:7][CH:4]23Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- extractionextracted with ether
- washthe organic phase was washed successively with 1 N Na2S2SO3 solution and brine
- dry with materialthe organic phase was then dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-9793b01deecc420c961ee622a595885d
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08829007B2
Reaction notes
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