p-Toluenesulfonic acid → 1-Bromo-2-(1E)-1-propen-1-ylbenzene

HRID 2297734Notes

Reaction equation

HRID 2297734 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH:19](O)[CH2:20][CH3:21].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH:19](/[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[Br:12])=[CH:20]\[CH3:21]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 134442791-(2-Bromophenyl)-1-propanol

Product 1

HCID 127154371-Bromo-2-(1E)-1-propen-1-ylbenzeneYield 803.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

p-Toluenesulfonic acid (30 mg) was added to a solution (50 mL) of 1-(2-bromophenyl)-1-propanol (5.55 g, 3.0 mmol) in toluene, followed by reflux for 5 hours. Next, the reaction solution was added to a saturated aqueous solution of sodium bicarbonate under ice-cooling to neutralize the reaction solution, and the mixture was then extracted with diethyl ether. After the extract was washed with a saturated brine and then dried over sodium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developed with diethyl ether/hexane=1/10) to give 2-((E)-1-propenyl)bromobenzene (4.75 g, yield 100%).

Workup

  1. temperatureby reflux for 5 hours
  2. temperaturecooling
  3. extractionthe mixture was then extracted with diethyl ether
  4. washAfter the extract was washed with a saturated brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (developed with diethyl ether/hexane=1/10)

Sources & evidence

ORD record
ord-7c180e5da27e43988a7462a41badf644
Source dataset
uspto-grants-2002_12
Patent number
US06492392B1

Reaction notes

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