Hydrogen Bromide → HCID 178525707, compound

HRID 1197330Notes

Reaction equation

HRID 1197330 reaction equation
[Br:1][C:2]([Br:14])=[CH:3][C@@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]([O:12]C)=[O:11])[CH2:6][CH2:5]1.Br>C(O)(=O)C>[Br:1][C:2]([Br:14])=[CH:3][C@@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]([OH:12])=[O:11])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 178501078HCID 178501078, compound

Product 1

HCID 178525707HCID 178525707, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

cis-Methyl 4-(2,2-dibromovinyl)cyclohexanecarboxylate (4 g) was heated to reflux in a solution of hydrobromic acid (48%, 20 ml) and acetic acid (40 ml). After heating for 4 hours the solvent was removed under reduced pressure. Water (50 ml) was added and the mixture extracted with diethyl ether. The ether extracts were extracted with sodium bicarbonate solution. The aqueous layer was then acidified and re-extracted with ether. The ethereal layer washed with brine and dried over anhydrous magnesium sulphate. Evaporation gave cis-4-(2,2-dibromovinyl)cyclohexanecarboxylic acid (3.6 g) as a pale yellow oil.

Workup

  1. temperatureAfter heating for 4 hours the solvent
  2. customwas removed under reduced pressure
  3. additionWater (50 ml) was added
  4. extractionthe mixture extracted with diethyl ether
  5. extractionThe ether extracts were extracted with sodium bicarbonate solution
  6. extractionre-extracted with ether
  7. washThe ethereal layer washed with brine
  8. dry with materialdried over anhydrous magnesium sulphate
  9. customEvaporation

Sources & evidence

ORD record
ord-3bfa487ebe634cfe998c4dbdf377e79e
Source dataset
uspto-grants-1992_05
Patent number
US05116862

Reaction notes

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