Sulfuric Acid → HCID 57591513, compound

HRID 1367682Notes

Reaction equation

HRID 1367682 reaction equation
[Br:1][C:2]1[CH:3]2[CH2:11][CH:6]([C:7](Br)(Br)[CH:8]=1)[CH2:5][CH2:4]2.C(#N)C.S(=O)(=O)(O)[OH:16].[OH-].[Na+]>ClC1C=CC=CC=1>[Br:1][C:2]1[CH:3]2[CH2:11][CH:6]([CH2:5][CH2:4]2)[C:7](=[O:16])[CH:8]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 574469862,4,4-Tribromobicyclo[3.2.1]oct-2-ene

Product 1

HCID 57591513HCID 57591513, compoundYield 6.3%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To a solution of 89.9 g (7.9% w/w, 100%=7.1 g, 20.6 mmol) of 2,4,4-tribromobicyclo[3.2.1]oct-2-ene in chlorobenzene there are added 100 ml of acetonitrile and 100 ml of 10% sulfuric acid and stirring is carried out for 50 minutes at ambient temperature. The pH is then adjusted to 7 using aqueous sodium hydroxide solution and the aqueous phase is separated off. The organic phase is washed with 50 ml of water and then dried using magnesium sulfate. After filtration and removal of the acetonitrile using a rotary evaporator, 57.8 g (88% of theory) of 4-bromo-bicyclo[3.2.1]oct-3-en-2-one are obtained as a 6.3% solution in chlorobenzene.

Workup

  1. customthe aqueous phase is separated off
  2. washThe organic phase is washed with 50 ml of water
  3. customdried
  4. filtrationAfter filtration and removal of the acetonitrile using
  5. customa rotary evaporator, 57.8 g (88% of theory) of 4-bromo-bicyclo[3.2.1]oct-3-en-2-one

Sources & evidence

ORD record
ord-4f83756732eb466384924c60575a1a7b
Source dataset
uspto-grants-2011_02
Patent number
US07893270B2

Reaction notes

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