1,3-Propanediol → 2-(4-Bromo-3-fluorophenyl)-1,3-dioxane

HRID 1177388Notes

Reaction equation

HRID 1177388 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[F:10].[CH2:11](O)[CH2:12][CH2:13][OH:14].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[O:14][CH2:13][CH2:12][CH2:11][O:7]2)=[CH:4][C:3]=1[F:10]

Participants

5

Reactant 3

HCID 104421,3-PropanediolHCID 521998p-Toluenesulfonic acid monohydrateHCID 27834114-Bromo-3-fluorobenzaldehyde

Product 1

HCID 671119942-(4-Bromo-3-fluorophenyl)-1,3-dioxane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Bromo-3-fluorobenzaldehyde (100.00 g, 492.6 mmol) was added to toluene (1 L). Propane-1,3-diol (42.72 mL, 591.1 mmol), and p-toluenesulfonic acid monohydrate (4.685 g, 24.63 mmol) were added to above and the reaction mixture was brought to reflux. The solvent (500 mL) was azeotroped off using a dean stark trap. The reaction mixture was cooled and extracted with sat. aqueous sodium bicarbonate (500 mL). The organics were dried over magnesium sulfate and concentrated in vacuo to give 2-(4-bromo-3-fluorophenyl)-1,3-dioxane as a white solid. MS (ESI) m/z: Calculated: 260.0/262.0; Observed: 260.9 (M++1).

Workup

  1. temperatureto reflux
  2. customThe solvent (500 mL) was azeotroped off
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with sat. aqueous sodium bicarbonate (500 mL)
  5. dry with materialThe organics were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-10ed149607a74ddca645e0b4687e5c6c
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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