p-Toluenesulfonic acid → 2-(4'-Bromo-3',5'-difluorophenyl)-5-pentyl-1,3-dioxane

HRID 1707524Notes

Reaction equation

HRID 1707524 reaction equation
[CH2:1]([CH:6]([CH2:9][OH:10])[CH2:7][OH:8])[CH2:2][CH2:3][CH2:4][CH3:5].[Br:11][C:12]1[C:19]([F:20])=[CH:18][C:15]([CH:16]=O)=[CH:14][C:13]=1[F:21].CC1C=CC(S(O)(=O)=O)=CC=1>ClCCl>[Br:11][C:12]1[C:19]([F:20])=[CH:18][C:15]([CH:16]2[O:10][CH2:9][CH:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:7][O:8]2)=[CH:14][C:13]=1[F:21]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 1175092-Pentyl-1,3-propanediolHCID 234437854-Bromo-3,5-difluorobenzaldehyde

Product 1

HCID 189615282-(4'-Bromo-3',5'-difluorophenyl)-5-pentyl-1,3-dioxaneYield 35.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10.8 g (0.074 mol) of 2-pentylpropane-1,3-diol, 16.3 g of 4-bromo-3,5-difluorobenzaldehyde and 0.7 g of TsOH were dissolved in 74 cm3 of dichloromethane, and was refluxed for 3 hours on a hot water bath with a Dean-Stark trap applied to remove the water formed. The reactant was washed in water, the dichloromethane was removed, and the residue was recrystallized from a mixture of acetone and methanol to obtain 9.1 g (0.026 mol) of 2-(4'-bromo-3',5'-difluorophenyl)-5-pentyl-1,3-dioxane.

Workup

  1. temperaturewas refluxed for 3 hours on a hot water bath with a Dean-Stark trap
  2. customto remove the water
  3. customformed
  4. washThe reactant was washed in water
  5. customthe dichloromethane was removed
  6. customthe residue was recrystallized from a mixture of acetone and methanol

Sources & evidence

ORD record
ord-c6efa1ae6cec4ad5abf91a8e1cc48f87
Source dataset
uspto-grants-1994_10
Patent number
US05354502

Reaction notes

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