Bromine → 6-Bromohexahydro-2h-3,5-methanocyclopenta[b]furan-2-one

HRID 75044

Reaction equation

HRID 75044 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]23

Participants

5

Reactant 3

HCID 24408BromineHCID 789495-Norbornene-2-carboxylic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 2636406-Bromohexahydro-2h-3,5-methanocyclopenta[b]furan-2-oneYield 67.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. extractionextracted with ether
  2. washthe organic phase was washed successively with 1 N Na2S2SO3 solution and brine
  3. dry with materialthe organic phase was then dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9793b01deecc420c961ee622a595885d
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Linked notes

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