p-Toluenesulfonic acid → 2-(2-Fluoro-6-iodo-phenyl)-[1,3]dioxane

HRID 2245283Notes

Reaction equation

HRID 2245283 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([I:10])[C:3]=1[CH:4]=[O:5].[CH2:11](O)[CH2:12][CH2:13][OH:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([I:10])[C:3]=1[CH:4]1[O:14][CH2:13][CH2:12][CH2:11][O:5]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 104421,3-PropanediolHCID 110969762-Fluoro-6-iodobenzaldehyde

Product 1

HCID 685501032-(2-Fluoro-6-iodo-phenyl)-[1,3]dioxaneYield 98.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Fluoro-6-iodo-benzaldehyde (3.0 g, 12 mmol), 1,3-propanediol (1.3 ml, 18 mmol), and para-toluenesulfonic acid (342 mg, 1.8 mmol) is heated at reflux in toluene (60 ml) using a Dean-Stark apparatus for 2 hours. The organic layer is washed with brine and dried over MgSO4 and evaporated to afford the desired compound (3.65 g).

Workup

  1. customfor 2 hours
  2. washThe organic layer is washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-f6d8481666b6409891eb7c832c162c2f
Source dataset
uspto-grants-2010_03
Patent number
US07683075B2

Reaction notes

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