p-Toluenesulfonic acid → 1,2-Difluoro-4-(prop-1-en-2-yl)benzene

HRID 1167706Notes

Reaction equation

HRID 1167706 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9](O)([CH3:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[F:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]([CH3:11])=[CH2:10])=[CH:3][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 108210712-(3,4-Difluorophenyl)propan-2-ol

Product 1

HCID 155252121,2-Difluoro-4-(prop-1-en-2-yl)benzene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(3,4-difluorophenyl)propan-2-ol (1.0 g, 5.8 mmol) in 40 mL benzene was added 0.1 g of p-toluenesulfonic acid and the solution was heated to 60° C. TLC analysis showed disappearance of the starting material. After cooling, the solution was extracted with EtOAc, washed with saturated NaHCO3, dried over Na2SO4, filtered and the solvent was removed in vacuo. 1,2-difluoro-4-isopropenyl-benzene was obtained as a yellow oil (0.82 g, 92% yield).

Workup

  1. temperatureAfter cooling
  2. extractionthe solution was extracted with EtOAc
  3. washwashed with saturated NaHCO3
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-68d80f066d674cbe92a06bae90410192
Source dataset
uspto-grants-2003_09
Patent number
US06620815B1

Reaction notes

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